BG107827A - Производни на 3-арилиндол и тяхното използване като св2 рецепторни антагонисти - Google Patents

Производни на 3-арилиндол и тяхното използване като св2 рецепторни антагонисти Download PDF

Info

Publication number: BG107827A
Authority: BG; Bulgaria
Prior art keywords: formula; compound; compounds; methyl; alkyl
Prior art date: 2000-11-22

Application number

BG107827A

Other languages

Bulgarian (bg)

English (en)

Inventor

Francis Barth

Christian Congy

Carole Guillaumont

Murielle Rinaldi

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.)

2000-11-22

Filing date

2003-05-19

Publication date

2004-01-30

2003-05-19 Application filed by Sanofi-Synthelabo filed Critical Sanofi-Synthelabo

2004-01-30 Publication of BG107827A publication Critical patent/BG107827A/bg

Links

239000000018 receptor agonist Substances 0.000 title 1
229940044601 receptor agonist Drugs 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 198
238000002360 preparation method Methods 0.000 claims abstract description 35
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
-1 tri-substituted phenyl Chemical group 0.000 claims description 93
238000000034 method Methods 0.000 claims description 69
239000000460 chlorine Substances 0.000 claims description 65
229910052739 hydrogen Inorganic materials 0.000 claims description 43
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 32
125000005843 halogen group Chemical group 0.000 claims description 31
239000001257 hydrogen Substances 0.000 claims description 31
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 31
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 25
229910052801 chlorine Inorganic materials 0.000 claims description 21
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 18
150000003839 salts Chemical class 0.000 claims description 18
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 18
239000013543 active substance Substances 0.000 claims description 15
239000012453 solvate Substances 0.000 claims description 15
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 13
150000004820 halides Chemical class 0.000 claims description 12
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 claims description 12
229910052740 iodine Inorganic materials 0.000 claims description 11
239000002253 acid Substances 0.000 claims description 9
125000001309 chloro group Chemical group Cl* 0.000 claims description 9
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 8
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 8
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
229930003827 cannabinoid Natural products 0.000 claims description 8
239000003557 cannabinoid Substances 0.000 claims description 8
239000003814 drug Substances 0.000 claims description 8
125000001041 indolyl group Chemical group 0.000 claims description 8
229910052794 bromium Inorganic materials 0.000 claims description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
150000002475 indoles Chemical class 0.000 claims description 7
239000002168 alkylating agent Substances 0.000 claims description 6
229940100198 alkylating agent Drugs 0.000 claims description 6
239000000546 pharmaceutical excipient Substances 0.000 claims description 6
101100533888 Hypocrea jecorina (strain QM6a) sor4 gene Proteins 0.000 claims description 5
101100533877 Hypocrea jecorina (strain QM6a) sor8 gene Proteins 0.000 claims description 5
239000004480 active ingredient Substances 0.000 claims description 5
150000001450 anions Chemical class 0.000 claims description 5
229910052736 halogen Inorganic materials 0.000 claims description 5
150000002367 halogens Chemical class 0.000 claims description 5
125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 4
125000004414 alkyl thio group Chemical group 0.000 claims description 4
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 4
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 4
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 4
125000001624 naphthyl group Chemical group 0.000 claims description 4
239000007800 oxidant agent Substances 0.000 claims description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
235000009518 sodium iodide Nutrition 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
150000002431 hydrogen Chemical class 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
229940124531 pharmaceutical excipient Drugs 0.000 claims description 3
101100516568 Caenorhabditis elegans nhr-7 gene Proteins 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
230000007170 pathology Effects 0.000 claims 1
102000009135 CB2 Cannabinoid Receptor Human genes 0.000 abstract description 3
108010073376 CB2 Cannabinoid Receptor Proteins 0.000 abstract description 3
229940121376 cannabinoid receptor agonist Drugs 0.000 abstract description 3
239000003537 cannabinoid receptor agonist Substances 0.000 abstract description 3
239000000243 solution Substances 0.000 description 74
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 72
239000000203 mixture Substances 0.000 description 71
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 60
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 57
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 40
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 38
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 29
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 29
XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 25
239000011541 reaction mixture Substances 0.000 description 25
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 19
WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 19
239000012074 organic phase Substances 0.000 description 17
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
239000000741 silica gel Substances 0.000 description 14
229910002027 silica gel Inorganic materials 0.000 description 14
238000003756 stirring Methods 0.000 description 14
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
229910052786 argon Inorganic materials 0.000 description 12
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 11
102000018208 Cannabinoid Receptor Human genes 0.000 description 10
108050007331 Cannabinoid receptor Proteins 0.000 description 10
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 10
239000012299 nitrogen atmosphere Substances 0.000 description 10
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
239000002585 base Substances 0.000 description 9
239000000047 product Substances 0.000 description 9
229920006395 saturated elastomer Polymers 0.000 description 9
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 9
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 8
201000010099 disease Diseases 0.000 description 8
102000005962 receptors Human genes 0.000 description 8
108020003175 receptors Proteins 0.000 description 8
229910000104 sodium hydride Inorganic materials 0.000 description 8
239000008346 aqueous phase Substances 0.000 description 7
229910052757 nitrogen Inorganic materials 0.000 description 7
238000010992 reflux Methods 0.000 description 7
239000000377 silicon dioxide Substances 0.000 description 7
239000002904 solvent Substances 0.000 description 7
239000003826 tablet Substances 0.000 description 7
YBONBWJSFMTXLE-UHFFFAOYSA-N 2,3-dichlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC(Cl)=C1Cl YBONBWJSFMTXLE-UHFFFAOYSA-N 0.000 description 6
XGLVDUUYFKXKPL-UHFFFAOYSA-N 2-(2-methoxyethoxy)-n,n-bis[2-(2-methoxyethoxy)ethyl]ethanamine Chemical compound COCCOCCN(CCOCCOC)CCOCCOC XGLVDUUYFKXKPL-UHFFFAOYSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
206010028980 Neoplasm Diseases 0.000 description 5
229940065144 cannabinoids Drugs 0.000 description 5
210000004027 cell Anatomy 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
230000005764 inhibitory process Effects 0.000 description 5
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
LVKCSZQWLOVUGB-UHFFFAOYSA-M magnesium;propane;bromide Chemical compound [Mg+2].[Br-].C[CH-]C LVKCSZQWLOVUGB-UHFFFAOYSA-M 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
239000011734 sodium Substances 0.000 description 5
YIJQQOHTYWFLQH-UHFFFAOYSA-N 7-chloro-2-methyl-1h-indole Chemical compound C1=CC(Cl)=C2NC(C)=CC2=C1 YIJQQOHTYWFLQH-UHFFFAOYSA-N 0.000 description 4
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 4
239000002775 capsule Substances 0.000 description 4
UAIZDWNSWGTKFZ-UHFFFAOYSA-L ethylaluminum(2+);dichloride Chemical compound CC[Al](Cl)Cl UAIZDWNSWGTKFZ-UHFFFAOYSA-L 0.000 description 4
238000000338 in vitro Methods 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
239000012044 organic layer Substances 0.000 description 4
239000000843 powder Substances 0.000 description 4
GNHPNQQIVWCDEU-UHFFFAOYSA-N 1-bromo-3-methylsulfanylpropane Chemical compound CSCCCBr GNHPNQQIVWCDEU-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
241000282412 Homo Species 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
108060008682 Tumor Necrosis Factor Proteins 0.000 description 3
102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
238000001990 intravenous administration Methods 0.000 description 3
210000004698 lymphocyte Anatomy 0.000 description 3
210000002540 macrophage Anatomy 0.000 description 3
230000002093 peripheral effect Effects 0.000 description 3
229920000642 polymer Polymers 0.000 description 3
239000001267 polyvinylpyrrolidone Substances 0.000 description 3
229920000036 polyvinylpyrrolidone Polymers 0.000 description 3
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
239000012312 sodium hydride Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
LLMLNAVBOAMOEE-UHFFFAOYSA-N 2,3-dichlorobenzaldehyde Chemical compound ClC1=CC=CC(C=O)=C1Cl LLMLNAVBOAMOEE-UHFFFAOYSA-N 0.000 description 2
HQMXRIGBXOFKIU-UHFFFAOYSA-N 2-bromobut-1-ene Chemical compound CCC(Br)=C HQMXRIGBXOFKIU-UHFFFAOYSA-N 0.000 description 2
BHNHHSOHWZKFOX-UHFFFAOYSA-N 2-methyl-1H-indole Chemical compound C1=CC=C2NC(C)=CC2=C1 BHNHHSOHWZKFOX-UHFFFAOYSA-N 0.000 description 2
UDBYPKMWCRZNJA-UHFFFAOYSA-N 2-methyl-7-propan-2-yl-1h-indole Chemical compound CC(C)C1=CC=CC2=C1NC(C)=C2 UDBYPKMWCRZNJA-UHFFFAOYSA-N 0.000 description 2
LULAYUGMBFYYEX-UHFFFAOYSA-N 3-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 2
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
IEPFVNLFBPBYMO-UHFFFAOYSA-N 7-bromo-2-ethyl-1h-indole Chemical compound C1=CC(Br)=C2NC(CC)=CC2=C1 IEPFVNLFBPBYMO-UHFFFAOYSA-N 0.000 description 2
YFEGQGALXHJBIQ-UHFFFAOYSA-N 7-bromo-2-methyl-1h-indole Chemical compound C1=CC(Br)=C2NC(C)=CC2=C1 YFEGQGALXHJBIQ-UHFFFAOYSA-N 0.000 description 2
WQJJAQXIXFDBDI-UHFFFAOYSA-N 7-ethyl-2-methyl-1h-indole Chemical compound CCC1=CC=CC2=C1NC(C)=C2 WQJJAQXIXFDBDI-UHFFFAOYSA-N 0.000 description 2
208000024827 Alzheimer disease Diseases 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
102100036214 Cannabinoid receptor 2 Human genes 0.000 description 2
244000025254 Cannabis sativa Species 0.000 description 2
229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
229920000858 Cyclodextrin Polymers 0.000 description 2
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 2
CTKXFMQHOOWWEB-UHFFFAOYSA-N Ethylene oxide/propylene oxide copolymer Chemical compound CCCOC(C)COCCO CTKXFMQHOOWWEB-UHFFFAOYSA-N 0.000 description 2
OHCQJHSOBUTRHG-KGGHGJDLSA-N FORSKOLIN Chemical compound O=C([C@@]12O)C[C@](C)(C=C)O[C@]1(C)[C@@H](OC(=O)C)[C@@H](O)[C@@H]1[C@]2(C)[C@@H](O)CCC1(C)C OHCQJHSOBUTRHG-KGGHGJDLSA-N 0.000 description 2
MFESCIUQSIBMSM-UHFFFAOYSA-N I-BCP Chemical compound ClCCCBr MFESCIUQSIBMSM-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
208000002193 Pain Diseases 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
101100369068 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) TDA1 gene Proteins 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
206010047700 Vomiting Diseases 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
230000010933 acylation Effects 0.000 description 2
238000005917 acylation reaction Methods 0.000 description 2
239000000443 aerosol Substances 0.000 description 2
150000008044 alkali metal hydroxides Chemical class 0.000 description 2
150000001350 alkyl halides Chemical class 0.000 description 2
229940054051 antipsychotic indole derivative Drugs 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
239000001768 carboxy methyl cellulose Substances 0.000 description 2
235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
239000008112 carboxymethyl-cellulose Substances 0.000 description 2
BGGXRVPCJUKHTQ-AHCAJXDVSA-L carumonam sodium Chemical compound [Na+].[Na+].O=C1N(S([O-])(=O)=O)[C@H](COC(=O)N)[C@@H]1NC(=O)C(=N/OCC([O-])=O)\C1=CSC(N)=N1 BGGXRVPCJUKHTQ-AHCAJXDVSA-L 0.000 description 2
HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 2
230000001684 chronic effect Effects 0.000 description 2
230000003111 delayed effect Effects 0.000 description 2
208000035475 disorder Diseases 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
235000003599 food sweetener Nutrition 0.000 description 2
239000007789 gas Substances 0.000 description 2
239000008187 granular material Substances 0.000 description 2
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
239000007943 implant Substances 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
238000007918 intramuscular administration Methods 0.000 description 2
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
239000007788 liquid Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
239000004005 microsphere Substances 0.000 description 2
POSMIGJZZDTBHR-UHFFFAOYSA-N n-[3-[6,7-dichloro-3-[2-fluoro-3-(trifluoromethyl)benzoyl]-2-methylindol-1-yl]propyl]methanesulfonamide Chemical compound C12=CC=C(Cl)C(Cl)=C2N(CCCNS(C)(=O)=O)C(C)=C1C(=O)C1=CC=CC(C(F)(F)F)=C1F POSMIGJZZDTBHR-UHFFFAOYSA-N 0.000 description 2
208000027831 neuroepithelial neoplasm Diseases 0.000 description 2
229940044519 poloxamer 188 Drugs 0.000 description 2
229920001993 poloxamer 188 Polymers 0.000 description 2
229920001223 polyethylene glycol Polymers 0.000 description 2
239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 2
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
229940068968 polysorbate 80 Drugs 0.000 description 2
229920000053 polysorbate 80 Polymers 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000011591 potassium Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
230000002265 prevention Effects 0.000 description 2
208000029340 primitive neuroectodermal tumor Diseases 0.000 description 2
230000002035 prolonged effect Effects 0.000 description 2
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 2
206010039073 rheumatoid arthritis Diseases 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
239000007921 spray Substances 0.000 description 2
238000007920 subcutaneous administration Methods 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
239000003765 sweetening agent Substances 0.000 description 2
208000011580 syndromic disease Diseases 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
239000006188 syrup Substances 0.000 description 2
230000000699 topical effect Effects 0.000 description 2
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 2
230000008673 vomiting Effects 0.000 description 2
239000000080 wetting agent Substances 0.000 description 2
CKUZHQGTQVKYQT-UHFFFAOYSA-N (2,3-dichlorophenyl)-(2-methyl-7-propan-2-yl-1h-indol-3-yl)methanone Chemical compound CC=1NC=2C(C(C)C)=CC=CC=2C=1C(=O)C1=CC=CC(Cl)=C1Cl CKUZHQGTQVKYQT-UHFFFAOYSA-N 0.000 description 1
PYUIMSUGZTTZJG-UHFFFAOYSA-N (2,3-dichlorophenyl)-(7-ethyl-2-methyl-1h-indol-3-yl)methanone Chemical compound CC=1NC=2C(CC)=CC=CC=2C=1C(=O)C1=CC=CC(Cl)=C1Cl PYUIMSUGZTTZJG-UHFFFAOYSA-N 0.000 description 1
RQLNBARFVGSQJC-UHFFFAOYSA-N (2,3-dichlorophenyl)-[1-(2-ethylsulfanylethyl)-2-methyl-7-propan-2-ylindol-3-yl]methanone Chemical compound C12=CC=CC(C(C)C)=C2N(CCSCC)C(C)=C1C(=O)C1=CC=CC(Cl)=C1Cl RQLNBARFVGSQJC-UHFFFAOYSA-N 0.000 description 1
JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
CDCBRHACUHPRHU-UHFFFAOYSA-N (7-bromo-2-ethyl-1h-indol-3-yl)-(2,3-dichlorophenyl)methanone Chemical compound CCC=1NC2=C(Br)C=CC=C2C=1C(=O)C1=CC=CC(Cl)=C1Cl CDCBRHACUHPRHU-UHFFFAOYSA-N 0.000 description 1
JCKFKSYROBMKEM-UHFFFAOYSA-N (7-bromo-2-methyl-1h-indol-3-yl)-(2,3-dichlorophenyl)methanone Chemical compound CC=1NC2=C(Br)C=CC=C2C=1C(=O)C1=CC=CC(Cl)=C1Cl JCKFKSYROBMKEM-UHFFFAOYSA-N 0.000 description 1
LPEYNILJWAUEDZ-LYPGVJLCSA-N (Z)-octadec-9-enoic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O.CCCCCCCC\C=C/CCCCCCCC(O)=O.CCCCCCCC\C=C/CCCCCCCC(O)=O.CCCCCCCC\C=C/CCCCCCCC(O)=O LPEYNILJWAUEDZ-LYPGVJLCSA-N 0.000 description 1
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
CMVQZRLQEOAYSW-UHFFFAOYSA-N 1,2-dichloro-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(Cl)=C1Cl CMVQZRLQEOAYSW-UHFFFAOYSA-N 0.000 description 1
ORPVVAKYSXQCJI-UHFFFAOYSA-N 1-bromo-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Br ORPVVAKYSXQCJI-UHFFFAOYSA-N 0.000 description 1
QMUUMVLJNYZYSS-UHFFFAOYSA-N 1-bromo-3-chloropropan-2-one Chemical compound ClCC(=O)CBr QMUUMVLJNYZYSS-UHFFFAOYSA-N 0.000 description 1
BNECODFCHDCLDN-UHFFFAOYSA-N 1-bromo-3-methylsulfonylpropane Chemical compound CS(=O)(=O)CCCBr BNECODFCHDCLDN-UHFFFAOYSA-N 0.000 description 1
JDYHPYHZVDTQLL-UHFFFAOYSA-N 1-chloro-1-ethylsulfanylethane Chemical compound CCSC(C)Cl JDYHPYHZVDTQLL-UHFFFAOYSA-N 0.000 description 1
BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 description 1
PXWYZLWEKCMTEZ-UHFFFAOYSA-N 1-ethyl-2-nitrobenzene Chemical compound CCC1=CC=CC=C1[N+]([O-])=O PXWYZLWEKCMTEZ-UHFFFAOYSA-N 0.000 description 1
BSMKYQUHXQAVKG-UHFFFAOYSA-N 1-nitro-2-propan-2-ylbenzene Chemical compound CC(C)C1=CC=CC=C1[N+]([O-])=O BSMKYQUHXQAVKG-UHFFFAOYSA-N 0.000 description 1
OGEQNKAKLVPHGS-UHFFFAOYSA-N 2-(7-chloro-2-methylindol-1-yl)ethanamine Chemical compound C1=CC(Cl)=C2N(CCN)C(C)=CC2=C1 OGEQNKAKLVPHGS-UHFFFAOYSA-N 0.000 description 1
RIKGRFSGIOOYEK-UHFFFAOYSA-N 2-fluoro-3-(trifluoromethyl)benzoyl chloride Chemical compound FC1=C(C(Cl)=O)C=CC=C1C(F)(F)F RIKGRFSGIOOYEK-UHFFFAOYSA-N 0.000 description 1
RQBKMMLKCNRZMS-UHFFFAOYSA-N 2-methylbutane-2-sulfonamide Chemical compound CCC(C)(C)S(N)(=O)=O RQBKMMLKCNRZMS-UHFFFAOYSA-N 0.000 description 1
HDMNMFRHIAMMED-UHFFFAOYSA-N 3-(7-chloro-2-methylindol-1-yl)propanenitrile Chemical compound C1=CC(Cl)=C2N(CCC#N)C(C)=CC2=C1 HDMNMFRHIAMMED-UHFFFAOYSA-N 0.000 description 1
HBKKQVYVJCYGIN-UHFFFAOYSA-N 3-(7-chloro-2-methylindol-1-yl)propanoic acid Chemical compound C1=CC(Cl)=C2N(CCC(O)=O)C(C)=CC2=C1 HBKKQVYVJCYGIN-UHFFFAOYSA-N 0.000 description 1
GPKDGVXBXQTHRY-UHFFFAOYSA-N 3-chloropropane-1-sulfonyl chloride Chemical compound ClCCCS(Cl)(=O)=O GPKDGVXBXQTHRY-UHFFFAOYSA-N 0.000 description 1
CZUGFKJYCPYHHV-UHFFFAOYSA-N 3-methylthiopropanol Chemical compound CSCCCO CZUGFKJYCPYHHV-UHFFFAOYSA-N 0.000 description 1
LKBNHTNNSBUPGC-UHFFFAOYSA-N 6,7-dichloro-1-(3-iodopropyl)-2-methylindole Chemical compound C1=C(Cl)C(Cl)=C2N(CCCI)C(C)=CC2=C1 LKBNHTNNSBUPGC-UHFFFAOYSA-N 0.000 description 1
PGKVRCDOBBACEN-UHFFFAOYSA-N 6,7-dichloro-2-methyl-1h-indole Chemical compound C1=C(Cl)C(Cl)=C2NC(C)=CC2=C1 PGKVRCDOBBACEN-UHFFFAOYSA-N 0.000 description 1
MVMRVNLBCYLBDG-UHFFFAOYSA-N 7-chloro-1-(1-chloropropyl)-2-methylindole Chemical compound C1=CC(Cl)=C2N(C(Cl)CC)C(C)=CC2=C1 MVMRVNLBCYLBDG-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
208000030507 AIDS Diseases 0.000 description 1
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
208000000884 Airway Obstruction Diseases 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
229920000856 Amylose Polymers 0.000 description 1
206010002383 Angina Pectoris Diseases 0.000 description 1
206010002556 Ankylosing Spondylitis Diseases 0.000 description 1
206010003267 Arthritis reactive Diseases 0.000 description 1
206010003571 Astrocytoma Diseases 0.000 description 1
201000001320 Atherosclerosis Diseases 0.000 description 1
208000023275 Autoimmune disease Diseases 0.000 description 1
208000035143 Bacterial infection Diseases 0.000 description 1
208000003174 Brain Neoplasms Diseases 0.000 description 1
206010006458 Bronchitis chronic Diseases 0.000 description 1
102000009132 CB1 Cannabinoid Receptor Human genes 0.000 description 1
108010073366 CB1 Cannabinoid Receptor Proteins 0.000 description 1
235000008697 Cannabis sativa Nutrition 0.000 description 1
235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 1
235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 1
208000024172 Cardiovascular disease Diseases 0.000 description 1
206010008748 Chorea Diseases 0.000 description 1
208000017667 Chronic Disease Diseases 0.000 description 1
208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 1
206010010741 Conjunctivitis Diseases 0.000 description 1
206010010744 Conjunctivitis allergic Diseases 0.000 description 1
208000011231 Crohn disease Diseases 0.000 description 1
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 description 1
208000006313 Delayed Hypersensitivity Diseases 0.000 description 1
238000007022 Delepine synthesis reaction Methods 0.000 description 1
238000010466 Delépine reaction Methods 0.000 description 1
SUZLHDUTVMZSEV-UHFFFAOYSA-N Deoxycoleonol Natural products C12C(=O)CC(C)(C=C)OC2(C)C(OC(=O)C)C(O)C2C1(C)C(O)CCC2(C)C SUZLHDUTVMZSEV-UHFFFAOYSA-N 0.000 description 1
206010012442 Dermatitis contact Diseases 0.000 description 1
235000019739 Dicalciumphosphate Nutrition 0.000 description 1
206010014561 Emphysema Diseases 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
238000005727 Friedel-Crafts reaction Methods 0.000 description 1
238000005642 Gabriel synthesis reaction Methods 0.000 description 1
208000018522 Gastrointestinal disease Diseases 0.000 description 1
201000004311 Gilles de la Tourette syndrome Diseases 0.000 description 1
208000010412 Glaucoma Diseases 0.000 description 1
201000005569 Gout Diseases 0.000 description 1
208000023105 Huntington disease Diseases 0.000 description 1
206010020772 Hypertension Diseases 0.000 description 1
208000013016 Hypoglycemia Diseases 0.000 description 1
208000001718 Immediate Hypersensitivity Diseases 0.000 description 1
206010061218 Inflammation Diseases 0.000 description 1
208000022559 Inflammatory bowel disease Diseases 0.000 description 1
206010065390 Inflammatory pain Diseases 0.000 description 1
102000000589 Interleukin-1 Human genes 0.000 description 1
108010002352 Interleukin-1 Proteins 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
208000019693 Lung disease Diseases 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
201000009906 Meningitis Diseases 0.000 description 1
XOGTZOOQQBDUSI-UHFFFAOYSA-M Mesna Chemical compound [Na+].[O-]S(=O)(=O)CCS XOGTZOOQQBDUSI-UHFFFAOYSA-M 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
229920000168 Microcrystalline cellulose Polymers 0.000 description 1
208000019695 Migraine disease Diseases 0.000 description 1
208000003926 Myelitis Diseases 0.000 description 1
206010029260 Neuroblastoma Diseases 0.000 description 1
208000008589 Obesity Diseases 0.000 description 1
208000001132 Osteoporosis Diseases 0.000 description 1
229910020667 PBr3 Inorganic materials 0.000 description 1
208000018737 Parkinson disease Diseases 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
201000004681 Psoriasis Diseases 0.000 description 1
208000028017 Psychotic disease Diseases 0.000 description 1
206010063897 Renal ischaemia Diseases 0.000 description 1
206010039085 Rhinitis allergic Diseases 0.000 description 1
241000283984 Rodentia Species 0.000 description 1
206010039966 Senile dementia Diseases 0.000 description 1
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
201000002661 Spondylitis Diseases 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
210000001744 T-lymphocyte Anatomy 0.000 description 1
208000000323 Tourette Syndrome Diseases 0.000 description 1
208000016620 Tourette disease Diseases 0.000 description 1
206010052779 Transplant rejections Diseases 0.000 description 1
206010045240 Type I hypersensitivity Diseases 0.000 description 1
NEBILETXTZKRTF-UHFFFAOYSA-N [7-bromo-1-(3-chloropropyl)-2-ethylindol-3-yl]-(2,3-dichlorophenyl)methanone Chemical compound C12=CC=CC(Br)=C2N(CCCCl)C(CC)=C1C(=O)C1=CC=CC(Cl)=C1Cl NEBILETXTZKRTF-UHFFFAOYSA-N 0.000 description 1
PHTWVVQWSFWASX-UHFFFAOYSA-N [7-bromo-1-(3-chloropropyl)-2-methylindol-3-yl]-(2,3-dichlorophenyl)methanone Chemical compound C12=CC=CC(Br)=C2N(CCCCl)C(C)=C1C(=O)C1=CC=CC(Cl)=C1Cl PHTWVVQWSFWASX-UHFFFAOYSA-N 0.000 description 1
XZQRMCHBSMTUFO-UHFFFAOYSA-N [7-bromo-2-ethyl-1-(3-iodopropyl)indol-3-yl]-(2,3-dichlorophenyl)methanone Chemical compound C12=CC=CC(Br)=C2N(CCCI)C(CC)=C1C(=O)C1=CC=CC(Cl)=C1Cl XZQRMCHBSMTUFO-UHFFFAOYSA-N 0.000 description 1
FGUDJJVPAVHCIT-UHFFFAOYSA-N [7-chloro-2-methyl-1-(3-methylsulfanylpropyl)indol-3-yl]-(2,3-dichlorophenyl)methanone Chemical compound C12=CC=CC(Cl)=C2N(CCCSC)C(C)=C1C(=O)C1=CC=CC(Cl)=C1Cl FGUDJJVPAVHCIT-UHFFFAOYSA-N 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
238000007259 addition reaction Methods 0.000 description 1
108060000200 adenylate cyclase Proteins 0.000 description 1
102000030621 adenylate cyclase Human genes 0.000 description 1
239000000556 agonist Substances 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000008051 alkyl sulfates Chemical class 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
125000001118 alkylidene group Chemical group 0.000 description 1
208000002205 allergic conjunctivitis Diseases 0.000 description 1
208000026935 allergic disease Diseases 0.000 description 1
201000010105 allergic rhinitis Diseases 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
230000003321 amplification Effects 0.000 description 1
206010002026 amyotrophic lateral sclerosis Diseases 0.000 description 1
230000002421 anti-septic effect Effects 0.000 description 1
229940064004 antiseptic throat preparations Drugs 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
206010003246 arthritis Diseases 0.000 description 1
208000006673 asthma Diseases 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
208000010216 atopic IgE responsiveness Diseases 0.000 description 1
208000024998 atopic conjunctivitis Diseases 0.000 description 1
210000003403 autonomic nervous system Anatomy 0.000 description 1
206010004398 benign neoplasm of skin Diseases 0.000 description 1
229940077388 benzenesulfonate Drugs 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 1
230000037396 body weight Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
210000004556 brain Anatomy 0.000 description 1
QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 1
206010006451 bronchitis Diseases 0.000 description 1
244000309464 bull Species 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
230000000747 cardiac effect Effects 0.000 description 1
239000000969 carrier Substances 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
238000002512 chemotherapy Methods 0.000 description 1
208000012601 choreatic disease Diseases 0.000 description 1
208000007451 chronic bronchitis Diseases 0.000 description 1
238000010367 cloning Methods 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
OHCQJHSOBUTRHG-UHFFFAOYSA-N colforsin Natural products OC12C(=O)CC(C)(C=C)OC1(C)C(OC(=O)C)C(O)C1C2(C)C(O)CCC1(C)C OHCQJHSOBUTRHG-UHFFFAOYSA-N 0.000 description 1
235000008504 concentrate Nutrition 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
208000018631 connective tissue disease Diseases 0.000 description 1
208000010247 contact dermatitis Diseases 0.000 description 1
239000013256 coordination polymer Substances 0.000 description 1
239000006184 cosolvent Substances 0.000 description 1
239000006071 cream Substances 0.000 description 1
230000001461 cytolytic effect Effects 0.000 description 1
210000001151 cytotoxic T lymphocyte Anatomy 0.000 description 1
CYQFCXCEBYINGO-IAGOWNOFSA-N delta1-THC Chemical group C1=C(C)CC[C@H]2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3[C@@H]21 CYQFCXCEBYINGO-IAGOWNOFSA-N 0.000 description 1
238000001514 detection method Methods 0.000 description 1
150000008050 dialkyl sulfates Chemical class 0.000 description 1
NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
229940038472 dicalcium phosphate Drugs 0.000 description 1
229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
UMNKXPULIDJLSU-UHFFFAOYSA-N dichlorofluoromethane Chemical compound FC(Cl)Cl UMNKXPULIDJLSU-UHFFFAOYSA-N 0.000 description 1
229940099364 dichlorofluoromethane Drugs 0.000 description 1
NPOMSUOUAZCMBL-UHFFFAOYSA-N dichloromethane;ethoxyethane Chemical compound ClCCl.CCOCC NPOMSUOUAZCMBL-UHFFFAOYSA-N 0.000 description 1
FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
XHFGWHUWQXTGAT-UHFFFAOYSA-N dimethylamine hydrochloride Natural products CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 1
IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 1
KZLUHGRPVSRSHI-UHFFFAOYSA-N dimethylmagnesium Chemical compound C[Mg]C KZLUHGRPVSRSHI-UHFFFAOYSA-N 0.000 description 1
MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 1
208000002173 dizziness Diseases 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000007908 dry granulation Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
206010015037 epilepsy Diseases 0.000 description 1
210000002745 epiphysis Anatomy 0.000 description 1
MVPICKVDHDWCJQ-UHFFFAOYSA-N ethyl 3-pyrrolidin-1-ylpropanoate Chemical compound CCOC(=O)CCN1CCCC1 MVPICKVDHDWCJQ-UHFFFAOYSA-N 0.000 description 1
229960003750 ethyl chloride Drugs 0.000 description 1
FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
210000003746 feather Anatomy 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
ZONYXWQDUYMKFB-UHFFFAOYSA-N flavanone Chemical compound O1C2=CC=CC=C2C(=O)CC1C1=CC=CC=C1 ZONYXWQDUYMKFB-UHFFFAOYSA-N 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000019634 flavors Nutrition 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
238000009472 formulation Methods 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
239000000499 gel Substances 0.000 description 1
208000005017 glioblastoma Diseases 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000012943 hotmelt Substances 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 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
UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
230000002218 hypoglycaemic effect Effects 0.000 description 1
230000002519 immonomodulatory effect Effects 0.000 description 1
230000036737 immune function Effects 0.000 description 1
208000026278 immune system disease Diseases 0.000 description 1
230000001506 immunosuppresive effect Effects 0.000 description 1
238000000099 in vitro assay Methods 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
230000002458 infectious effect Effects 0.000 description 1
208000027866 inflammatory disease Diseases 0.000 description 1
230000002757 inflammatory effect Effects 0.000 description 1
230000004054 inflammatory process Effects 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
230000004410 intraocular pressure Effects 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
238000002372 labelling Methods 0.000 description 1
239000008101 lactose Substances 0.000 description 1
229960001375 lactose Drugs 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
206010025135 lupus erythematosus Diseases 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
229910001623 magnesium bromide Inorganic materials 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
229960001855 mannitol Drugs 0.000 description 1
239000000463 material Substances 0.000 description 1
201000001441 melanoma Diseases 0.000 description 1
206010027191 meningioma Diseases 0.000 description 1
229960004635 mesna Drugs 0.000 description 1
HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 description 1
239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
235000010270 methyl p-hydroxybenzoate Nutrition 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
239000008108 microcrystalline cellulose Substances 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000003226 mitogen Substances 0.000 description 1
JFCHSQDLLFJHOA-UHFFFAOYSA-N n,n-dimethylsulfamoyl chloride Chemical compound CN(C)S(Cl)(=O)=O JFCHSQDLLFJHOA-UHFFFAOYSA-N 0.000 description 1
YMIFUSZFTRWYBF-UHFFFAOYSA-N n-[3-(6,7-dichloro-2-methylindol-1-yl)propyl]methanesulfonamide Chemical compound C1=C(Cl)C(Cl)=C2N(CCCNS(C)(=O)=O)C(C)=CC2=C1 YMIFUSZFTRWYBF-UHFFFAOYSA-N 0.000 description 1
LGAZPRPAQGWYOX-UHFFFAOYSA-N n-[3-[7-bromo-3-(2,3-dichlorobenzoyl)-2-ethylindol-1-yl]propyl]methanesulfonamide Chemical compound C12=CC=CC(Br)=C2N(CCCNS(C)(=O)=O)C(CC)=C1C(=O)C1=CC=CC(Cl)=C1Cl LGAZPRPAQGWYOX-UHFFFAOYSA-N 0.000 description 1
XUXSBTKOIPCCIC-UHFFFAOYSA-N n-[3-[7-chloro-3-[2-fluoro-3-(trifluoromethyl)phenyl]-2-methylindol-1-yl]propyl]methanesulfonamide Chemical compound C12=CC=CC(Cl)=C2N(CCCNS(C)(=O)=O)C(C)=C1C1=CC=CC(C(F)(F)F)=C1F XUXSBTKOIPCCIC-UHFFFAOYSA-N 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-M naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-M 0.000 description 1
208000004296 neuralgia Diseases 0.000 description 1
208000021722 neuropathic pain Diseases 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
238000003199 nucleic acid amplification method Methods 0.000 description 1
235000020824 obesity Nutrition 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
239000012053 oil suspension Substances 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
201000008482 osteoarthritis Diseases 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
208000003154 papilloma Diseases 0.000 description 1
230000003071 parasitic effect Effects 0.000 description 1
239000002831 pharmacologic agent Substances 0.000 description 1
IPNPIHIZVLFAFP-UHFFFAOYSA-N phosphorus tribromide Chemical compound BrP(Br)Br IPNPIHIZVLFAFP-UHFFFAOYSA-N 0.000 description 1
210000004180 plasmocyte Anatomy 0.000 description 1
ZDHURYWHEBEGHO-UHFFFAOYSA-N potassiopotassium Chemical compound [K].[K] ZDHURYWHEBEGHO-UHFFFAOYSA-N 0.000 description 1
150000003109 potassium Chemical class 0.000 description 1
229910000027 potassium carbonate Inorganic materials 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
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 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
210000002307 prostate Anatomy 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
230000000506 psychotropic effect Effects 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
208000002574 reactive arthritis Diseases 0.000 description 1
208000023504 respiratory system disease Diseases 0.000 description 1
230000004044 response Effects 0.000 description 1
239000012047 saturated solution Substances 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
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
229940045902 sodium stearyl fumarate Drugs 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000007909 solid dosage form Substances 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
229940032147 starch Drugs 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
238000013268 sustained release Methods 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
ODLHGICHYURWBS-LKONHMLTSA-N trappsol cyclo Chemical compound CC(O)COC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)COCC(O)C)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1COCC(C)O ODLHGICHYURWBS-LKONHMLTSA-N 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
GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
230000003612 virological effect Effects 0.000 description 1
238000005550 wet granulation Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/12—Radicals substituted by oxygen atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/04—Drugs for skeletal disorders for non-specific disorders of the connective tissue
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/06—Antigout agents, e.g. antihyperuricemic or uricosuric agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/04—Drugs for disorders of the muscular or neuromuscular system for myasthenia gravis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/16—Otologicals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P29/02—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID] without antiinflammatory effect
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/06—Antianaemics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Public Health (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Physical Education & Sports Medicine (AREA)
Rheumatology (AREA)
Pain & Pain Management (AREA)
Orthopedic Medicine & Surgery (AREA)
Pulmonology (AREA)
Immunology (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Hematology (AREA)
Heart & Thoracic Surgery (AREA)
Diabetes (AREA)
Virology (AREA)
Psychiatry (AREA)
Cardiology (AREA)
Tropical Medicine & Parasitology (AREA)
Dermatology (AREA)
Urology & Nephrology (AREA)
Hospice & Palliative Care (AREA)
Psychology (AREA)
Ophthalmology & Optometry (AREA)
Obesity (AREA)
AIDS & HIV (AREA)

BG107827A 2000-11-22 2003-05-19 Производни на 3-арилиндол и тяхното използване като св2 рецепторни антагонисти BG107827A (bg)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR0015158A FR2816938B1 (fr)	2000-11-22	2000-11-22	Derives de 3-aroylindole, leur procede de preparation et les compositions pharmaceutiques en contenant
PCT/FR2001/003665 WO2002042269A1 (fr)	2000-11-22	2001-11-21	Derives de 3-aroylindole et leur utilisation en tant qu'agonistes des recepteurs cb2

Publications (1)

Publication Number	Publication Date
BG107827A true BG107827A (bg)	2004-01-30

Family

ID=8856819

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BG107827A BG107827A (bg)	2000-11-22	2003-05-19	Производни на 3-арилиндол и тяхното използване като св2 рецепторни антагонисти

Country Status (32)

Country	Link
US (1)	US6995184B2 (et)
EP (1)	EP1339679B1 (et)
JP (1)	JP4264258B2 (et)
KR (1)	KR20030048161A (et)
CN (1)	CN1234688C (et)
AR (1)	AR033594A1 (et)
AT (1)	ATE301638T1 (et)
AU (1)	AU2002222001A1 (et)
BG (1)	BG107827A (et)
BR (1)	BR0115580A (et)
CA (1)	CA2427444A1 (et)
CZ (1)	CZ20031392A3 (et)
DE (1)	DE60112607T2 (et)
DK (1)	DK1339679T3 (et)
DZ (1)	DZ3443A1 (et)
EA (1)	EA005854B1 (et)
EE (1)	EE200300244A (et)
ES (1)	ES2247201T3 (et)
FR (1)	FR2816938B1 (et)
HR (1)	HRP20030417A2 (et)
HU (1)	HUP0400561A2 (et)
IL (1)	IL155634A0 (et)
IS (1)	IS6802A (et)
MA (1)	MA26959A1 (et)
MX (1)	MXPA03004549A (et)
NO (1)	NO20031952L (et)
NZ (1)	NZ525609A (et)
PL (1)	PL362276A1 (et)
SK (1)	SK6042003A3 (et)
TW (1)	TWI224592B (et)
WO (1)	WO2002042269A1 (et)
ZA (1)	ZA200303728B (et)

Families Citing this family (37)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
TW200407110A (en) *	2001-11-23	2004-05-16	Astrazeneca Ab	New use for the treatment of gastroesophageal reflux disease
JP2005533748A (ja)	2002-03-08	2005-11-10	シグナルファーマシューティカルズ，インコーポレイテッド	増殖性障害および癌を治療、予防、または管理するための併用療法
EP1509250B1 (en) *	2002-06-06	2008-05-07	Yissum Research Development Company Of The Hebrew University Of Jerusalem	Methods compositions and articles of manufacture for modulating bone growth
WO2004012671A2 (en)	2002-08-02	2004-02-12	Merck & Co., Inc.	Substituted furo [2,3-b] pyridine derivatives
FR2843964B1 (fr) *	2002-08-29	2004-10-01	Sanofi Synthelabo	Derives de dioxane-2-alkylcarbamates, leur preparation et leur application en therapeutique
FR2847899B1 (fr)	2002-11-29	2006-04-28	Sanofi Synthelabo	Derives d'indole-3-carboxamide, leur preparation et leur application en therapeutique
FR2854633B1 (fr) *	2003-05-07	2005-06-24	Sanofi Synthelabo	Derives de piperidinyl-et piperazinyl-alkylcarbamates, leur preparation et leur application en therapeutique
FR2856684B1 (fr)	2003-06-26	2008-04-11	Sanofi Synthelabo	Derives de diphenylpyridine, leur preparation et leur application en therapeutique
FR2865205B1 (fr) *	2004-01-16	2006-02-24	Sanofi Synthelabo	Derives de type aryloxyalkylcarbamates, leur preparation et leur application en therapeutique
CA2571679A1 (en) *	2004-06-22	2005-12-29	Pharmos Limited	Use of cb2 receptors agonists for the treatment of huntington's disease
CA2586011C (en)	2004-07-12	2011-07-19	Cadila Healthcare Limited	Tricyclic pyrazole derivatives as cannabinoid receptor modulators
US20060025448A1 (en)	2004-07-22	2006-02-02	Cadila Healthcare Limited	Hair growth stimulators
JP2008520719A (ja) *	2004-11-22	2008-06-19	スレショルドファーマシューティカルズインコーポレイティッド	チューブリン結合抗癌剤およびそれらのプロドラッグ
US7560481B2 (en)	2004-12-21	2009-07-14	Abbott Laboratories	Indoles are cannabinoid receptor ligands
FR2893615B1 (fr) *	2005-11-18	2008-03-07	Sanofi Aventis Sa	Derives de 3-acylindole, leur preparation et leur application en therapeutique
RU2306906C1 (ru) *	2006-04-21	2007-09-27	Федеральное государственное учреждение "Межотраслевой научно-технический комплекс "Микрохирургия глаза" имени академика С.Н. Федорова Федерального агентства по здравоохранению и социальному развитию"	Способ повышения зрительных функций при сублюксации хрусталика в случаях нарушения обмена в системе соединительной ткани
US8841334B2 (en)	2006-05-31	2014-09-23	Abbvie Inc.	Compounds as cannabinoid receptor ligands and uses thereof
JP2009538933A (ja)	2006-05-31	2009-11-12	アボット・ラボラトリーズ	カンナビノイド受容体リガンドとしての化合物およびその使用
GB0702862D0 (en) *	2007-02-14	2007-03-28	Univ Aberdeen	Therapeutic compounds
CN101765594A (zh)	2007-03-28	2010-06-30	雅培制药有限公司	作为大麻素受体配体的1,3-噻唑-2(3h)-亚基化合物
US7872033B2 (en) *	2007-04-17	2011-01-18	Abbott Laboratories	Compounds as cannabinoid receptor ligands
FR2915199B1 (fr) *	2007-04-18	2010-01-22	Sanofi Aventis	Derives de triazolopyridine-carboxamides et triazolopyrimidine-carboxamides, leur preparation et leur application en therapeutique.
WO2008144360A1 (en) *	2007-05-18	2008-11-27	Abbott Laboratories	Novel compounds as cannabinoid receptor ligands
US9193713B2 (en) *	2007-10-12	2015-11-24	Abbvie Inc.	Compounds as cannabinoid receptor ligands
FR2933697B1 (fr)	2008-07-11	2010-08-13	Sanofi Aventis	Derives de 1-benzyl-cinnolin-4-(1h)-one substitues, leur preparation et leur application en therapeutique
US8846730B2 (en)	2008-09-08	2014-09-30	Abbvie Inc.	Compounds as cannabinoid receptor ligands
US8188135B2 (en)	2008-09-16	2012-05-29	Abbott Laboratories	Compounds as cannabinoid receptor ligands
PA8854001A1 (es)	2008-12-16	2010-07-27	Abbott Lab	Compuestos novedosos como ligandos de receptores de canabinoides
FR2941696B1 (fr)	2009-02-05	2011-04-15	Sanofi Aventis	Derives d'azaspiranyl-alkylcarbamates d'heterocycles a 5 chainons, leur preparation et leur application en therapeutique
FR2945533B1 (fr)	2009-05-12	2011-05-27	Sanofi Aventis	Derives de cyclopenta°c!pyrrolyl-alkylcarbamates d'heterocycles a 5 chainons, leur preparation et leur application en therapeutique
US20120277296A1 (en)	2009-07-23	2012-11-01	Sophie Lotersztajn	Selective CB2 Receptor Agonists for Use in the Prevention or Treatment of Alcoholic Liver Disease
FR2950055A1 (fr)	2009-09-17	2011-03-18	Sanofi Aventis	Derives de 3-amino-cinnolin-4(1h)-one substitues, leur preparation et leur application en therapeutique
US20130178453A1 (en) *	2010-02-09	2013-07-11	Ironwood Pharmaceuticals, Inc.	Cannabinoid Agonists
FR2983859B1 (fr)	2011-12-12	2014-01-17	Sanofi Sa	Derives de 1,3,5-triazine-2-amine, leur preparation et leur application en diagnostique et en therapeutique
CN105899948A (zh) *	2013-11-28	2016-08-24	联邦科学技术研究组织	检测疟原虫感染的方法
CN108794379A (zh) *	2017-04-26	2018-11-13	华东师范大学	1h-吲哚-2-甲酰胺衍生物及其制备方法和应用
WO2022128050A1 (en)	2020-12-14	2022-06-23	Symrise Ag	Medicament for fighting inflammation and pain

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5532237A (en) *	1995-02-15	1996-07-02	Merck Frosst Canada, Inc.	Indole derivatives with affinity for the cannabinoid receptor
FR2735774B1 (fr) *	1995-06-21	1997-09-12	Sanofi Sa	Utilisation de composes agonistes du recepteur cb2 humain pour la preparation de medicaments immunomodulateurs, nouveaux composes agonistes du recepteur cb2 et les compositions pharmaceutiques les contenant
EP1223929B1 (en) *	1999-10-18	2006-08-23	The University Of Connecticut	Cannabimimetic indole derivatives

2000
- 2000-11-22 FR FR0015158A patent/FR2816938B1/fr not_active Expired - Fee Related
2001
- 2001-11-21 US US10/416,617 patent/US6995184B2/en not_active Expired - Fee Related
- 2001-11-21 KR KR10-2003-7006862A patent/KR20030048161A/ko not_active Withdrawn
- 2001-11-21 CA CA002427444A patent/CA2427444A1/fr not_active Abandoned
- 2001-11-21 BR BR0115580-6A patent/BR0115580A/pt not_active IP Right Cessation
- 2001-11-21 AT AT01997476T patent/ATE301638T1/de not_active IP Right Cessation
- 2001-11-21 DE DE60112607T patent/DE60112607T2/de not_active Expired - Lifetime
- 2001-11-21 DK DK01997476T patent/DK1339679T3/da active
- 2001-11-21 AR ARP010105425A patent/AR033594A1/es not_active Application Discontinuation
- 2001-11-21 HR HR20030417A patent/HRP20030417A2/hr not_active Application Discontinuation
- 2001-11-21 JP JP2002544405A patent/JP4264258B2/ja not_active Expired - Fee Related
- 2001-11-21 NZ NZ525609A patent/NZ525609A/en unknown
- 2001-11-21 EE EEP200300244A patent/EE200300244A/et unknown
- 2001-11-21 HU HU0400561A patent/HUP0400561A2/hu unknown
- 2001-11-21 EP EP01997476A patent/EP1339679B1/fr not_active Expired - Lifetime
- 2001-11-21 IL IL15563401A patent/IL155634A0/xx unknown
- 2001-11-21 EA EA200300453A patent/EA005854B1/ru not_active IP Right Cessation
- 2001-11-21 ES ES01997476T patent/ES2247201T3/es not_active Expired - Lifetime
- 2001-11-21 WO PCT/FR2001/003665 patent/WO2002042269A1/fr not_active Ceased
- 2001-11-21 MX MXPA03004549A patent/MXPA03004549A/es active IP Right Grant
- 2001-11-21 CN CNB018211755A patent/CN1234688C/zh not_active Expired - Fee Related
- 2001-11-21 SK SK604-2003A patent/SK6042003A3/sk unknown
- 2001-11-21 DZ DZ013443A patent/DZ3443A1/fr active
- 2001-11-21 AU AU2002222001A patent/AU2002222001A1/en not_active Abandoned
- 2001-11-21 CZ CZ20031392A patent/CZ20031392A3/cs unknown
- 2001-11-21 PL PL01362276A patent/PL362276A1/xx not_active Application Discontinuation
- 2001-11-22 TW TW090128947A patent/TWI224592B/zh active
2003
- 2003-04-29 NO NO20031952A patent/NO20031952L/no unknown
- 2003-04-30 IS IS6802A patent/IS6802A/is unknown
- 2003-05-13 MA MA27157A patent/MA26959A1/fr unknown
- 2003-05-14 ZA ZA200303728A patent/ZA200303728B/en unknown
- 2003-05-19 BG BG107827A patent/BG107827A/bg unknown

Also Published As

Publication number	Publication date
CN1234688C (zh)	2006-01-04
ES2247201T3 (es)	2006-03-01
FR2816938A1 (fr)	2002-05-24
IL155634A0 (en)	2003-11-23
EP1339679A1 (fr)	2003-09-03
MA26959A1 (fr)	2004-12-20
ATE301638T1 (de)	2005-08-15
EA200300453A1 (ru)	2003-10-30
ZA200303728B (en)	2004-05-14
DE60112607D1 (de)	2005-09-15
EP1339679B1 (fr)	2005-08-10
AR033594A1 (es)	2003-12-26
WO2002042269A1 (fr)	2002-05-30
FR2816938B1 (fr)	2003-01-03
MXPA03004549A (es)	2004-03-26
US20040034090A1 (en)	2004-02-19
HRP20030417A2 (en)	2003-08-31
DK1339679T3 (da)	2005-12-12
DZ3443A1 (fr)	2002-05-30
PL362276A1 (en)	2004-10-18
NO20031952D0 (no)	2003-04-29
KR20030048161A (ko)	2003-06-18
CZ20031392A3 (cs)	2003-09-17
NO20031952L (no)	2003-07-22
NZ525609A (en)	2004-11-26
CA2427444A1 (fr)	2002-05-30
AU2002222001A1 (en)	2002-06-03
US6995184B2 (en)	2006-02-07
IS6802A (is)	2003-04-30
JP2004514668A (ja)	2004-05-20
EA005854B1 (ru)	2005-06-30
CN1483023A (zh)	2004-03-17
HUP0400561A2 (hu)	2004-07-28
EE200300244A (et)	2003-10-15
JP4264258B2 (ja)	2009-05-13
SK6042003A3 (en)	2003-12-02
DE60112607T2 (de)	2006-06-14
BR0115580A (pt)	2003-09-09
TWI224592B (en)	2004-12-01

Publication	Publication Date	Title
BG107827A (bg)	2004-01-30	Производни на 3-арилиндол и тяхното използване като св2 рецепторни антагонисти
RU2200736C2 (ru)	2003-03-20	Применение соединений-агонистов человеческого рецептора cb2 для получения лекарственных иммуномодуляторов, новые соединения-агонисты рецептора cb2 и фармацевтические композиции на их основе
FI78466B (fi)	1989-04-28	Foerfarande foer framstaellning av farmakologiskt verksamma indolderivat.
AU2003283265B2 (en)	2009-03-05	4-piperazinyl benzenesulfonyl indoles with 5-HT6 receptor affinity
US6514968B1 (en)	2003-02-04	Aminoalkoxy carbazoles for the treatment of cns diseases
CA2211836A1 (en)	1996-08-22	Indole derivatives with affinity for the cannabinoid receptor
CZ297667B6 (cs)	2007-02-28	Derivát pyrazolkarboxylové kyseliny, zpusob jeho prípravy a farmaceutické prostredky, které ho obsahují
EP1507758B1 (fr)	2005-11-02	Derives d'indole et leur utilisation en tant que ligands des recepteurs cb2
CH667454A5 (fr)	1988-10-14	Derives d'indoles.
JP2003519225A (ja)	2003-06-17	４−フェニル−１−ピペラジニル、−ピペリジニル、および−テトラヒドロピリジル誘導体
KR100349634B1 (ko)	2003-01-08	인돌유도체및이를함유하는제제
JP2003519683A (ja)	2003-06-24	Ｍｃｐ−１受容体アンタゴニストとしてのインドール誘導体
JP5106410B2 (ja)	2012-12-26	３−アシルインドール誘導体、これらの調製および治療的使用
JP2003519684A (ja)	2003-06-24	Ｍｃｐ−１レセプターアンタゴニストとしてのインドール誘導体
WO1995025731A1 (fr)	1995-09-28	NOUVELLES 3-(φ-(4-BENZOYLPIPERIDINO)ALCOYL)-4H-BENZOPYRAN-4-ONES, LEUR PREPARATION ET LEUR APPLICATION EN THERAPEUTIQUE