ZA200303728B - 3-arlindole derivatives and their use as CB 2 receptor agonists. - Google Patents
3-arlindole derivatives and their use as CB 2 receptor agonists. Download PDFInfo
- Publication number
- ZA200303728B ZA200303728B ZA200303728A ZA200303728A ZA200303728B ZA 200303728 B ZA200303728 B ZA 200303728B ZA 200303728 A ZA200303728 A ZA 200303728A ZA 200303728 A ZA200303728 A ZA 200303728A ZA 200303728 B ZA200303728 B ZA 200303728B
- Authority
- ZA
- South Africa
- Prior art keywords
- formula
- compound
- alkyl
- halogen atom
- treated
- Prior art date
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- 239000000018 receptor agonist Substances 0.000 title 1
- 229940044601 receptor agonist Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 90
- 125000000217 alkyl group Chemical group 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 29
- 125000005843 halogen group Chemical group 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 26
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 18
- 229910052801 chlorine Inorganic materials 0.000 claims description 14
- 239000000460 chlorine Substances 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- -1 methylsulphanyl Chemical group 0.000 claims description 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 11
- 102000018208 Cannabinoid Receptor Human genes 0.000 claims description 11
- 108050007331 Cannabinoid receptor Proteins 0.000 claims description 11
- 239000012453 solvate Substances 0.000 claims description 10
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 claims description 9
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 8
- 150000004820 halides Chemical class 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000001041 indolyl group Chemical group 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 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
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 150000001450 anions Chemical class 0.000 claims description 4
- 229910052794 bromium Inorganic materials 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
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 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
- 239000003814 drug Substances 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 235000009518 sodium iodide Nutrition 0.000 claims description 3
- 102000007399 Nuclear hormone receptor Human genes 0.000 claims 3
- 108020005497 Nuclear hormone receptor Proteins 0.000 claims 3
- 229940100198 alkylating agent Drugs 0.000 claims 2
- 239000002168 alkylating agent Substances 0.000 claims 2
- 230000007170 pathology Effects 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 229940124531 pharmaceutical excipient Drugs 0.000 claims 1
- 239000002904 solvent Substances 0.000 description 5
- 239000002585 base Substances 0.000 description 4
- 229930003827 cannabinoid Natural products 0.000 description 4
- 239000003557 cannabinoid Substances 0.000 description 4
- 229940065144 cannabinoids Drugs 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
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- 238000006243 chemical reaction Methods 0.000 description 3
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- 244000025254 Cannabis sativa Species 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
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- 125000001424 substituent group Chemical group 0.000 description 2
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- 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
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 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
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
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- 108091006027 G proteins Proteins 0.000 description 1
- 102000030782 GTP binding Human genes 0.000 description 1
- 108091000058 GTP-Binding Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- 102000000589 Interleukin-1 Human genes 0.000 description 1
- 108010002352 Interleukin-1 Proteins 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical compound CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
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- 239000007983 Tris buffer Substances 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 125000001118 alkylidene group Chemical group 0.000 description 1
- 230000003321 amplification Effects 0.000 description 1
- 229940054051 antipsychotic indole derivative Drugs 0.000 description 1
- 210000003719 b-lymphocyte Anatomy 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
- 230000015572 biosynthetic process Effects 0.000 description 1
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- 210000004556 brain Anatomy 0.000 description 1
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- 125000004432 carbon atom Chemical group C* 0.000 description 1
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- 230000001461 cytolytic effect Effects 0.000 description 1
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- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 description 1
- 229940079593 drug 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
- 230000001747 exhibiting effect Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229940050410 gluconate Drugs 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
- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 1
- 230000002519 immonomodulatory effect Effects 0.000 description 1
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- 150000002475 indoles Chemical class 0.000 description 1
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- 238000002955 isolation Methods 0.000 description 1
- 150000002576 ketones Chemical class 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
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- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
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- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 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
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FR0015158A FR2816938B1 (fr) | 2000-11-22 | 2000-11-22 | Derives de 3-aroylindole, leur procede de preparation et les compositions pharmaceutiques en contenant |
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ZA200303728B true ZA200303728B (en) | 2004-05-14 |
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ZA200303728A ZA200303728B (en) | 2000-11-22 | 2003-05-14 | 3-arlindole derivatives and their use as CB 2 receptor agonists. |
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EP (1) | EP1339679B1 (ko) |
JP (1) | JP4264258B2 (ko) |
KR (1) | KR20030048161A (ko) |
CN (1) | CN1234688C (ko) |
AR (1) | AR033594A1 (ko) |
AT (1) | ATE301638T1 (ko) |
AU (1) | AU2002222001A1 (ko) |
BG (1) | BG107827A (ko) |
BR (1) | BR0115580A (ko) |
CA (1) | CA2427444A1 (ko) |
CZ (1) | CZ20031392A3 (ko) |
DE (1) | DE60112607T2 (ko) |
DK (1) | DK1339679T3 (ko) |
DZ (1) | DZ3443A1 (ko) |
EA (1) | EA005854B1 (ko) |
EE (1) | EE200300244A (ko) |
ES (1) | ES2247201T3 (ko) |
FR (1) | FR2816938B1 (ko) |
HR (1) | HRP20030417A2 (ko) |
HU (1) | HUP0400561A2 (ko) |
IL (1) | IL155634A0 (ko) |
IS (1) | IS6802A (ko) |
MA (1) | MA26959A1 (ko) |
MX (1) | MXPA03004549A (ko) |
NO (1) | NO20031952L (ko) |
NZ (1) | NZ525609A (ko) |
PL (1) | PL362276A1 (ko) |
SK (1) | SK6042003A3 (ko) |
TW (1) | TWI224592B (ko) |
WO (1) | WO2002042269A1 (ko) |
ZA (1) | ZA200303728B (ko) |
Families Citing this family (35)
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TW200407110A (en) * | 2001-11-23 | 2004-05-16 | Astrazeneca Ab | New use for the treatment of gastroesophageal reflux disease |
JP2006517194A (ja) | 2002-06-06 | 2006-07-20 | イッサム リサーチ ディベロップメント カンパニー オブ ザ ヘブリュー ユニバーシティ オブ エルサレム | 骨成長を調節するための方法、組成物および製造物 |
ATE375349T1 (de) | 2002-08-02 | 2007-10-15 | Merck & Co Inc | Substituierte furo(2,3-b)pyridin derivate |
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 |
KR20070041717A (ko) | 2004-07-12 | 2007-04-19 | 카딜라 핼쓰캐어 리미티드 | 카나비노이드 수용체 조절자인 트리시클릭 피라졸 유도체들 |
US20060025448A1 (en) | 2004-07-22 | 2006-02-02 | Cadila Healthcare Limited | Hair growth stimulators |
CA2587210A1 (en) * | 2004-11-22 | 2006-06-01 | Threshold Pharmaceuticals, Inc. | Tubulin binding anti cancer agents and prodrugs thereof |
EP1833824B1 (en) * | 2004-12-21 | 2016-08-03 | AbbVie Inc. | 3-cycloalkylcarbonyl indoles as 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 |
CA2647598A1 (en) * | 2006-05-31 | 2007-12-06 | Abbott Laboratories | Compounds as cannabinoid receptor ligands and uses thereof |
US8841334B2 (en) * | 2006-05-31 | 2014-09-23 | Abbvie Inc. | Compounds as cannabinoid receptor ligands and uses thereof |
GB0702862D0 (en) * | 2007-02-14 | 2007-03-28 | Univ Aberdeen | Therapeutic compounds |
CA2681586A1 (en) | 2007-03-28 | 2008-10-09 | Abbott Laboratories | 1, 3-thiazol-2 (3h) -ylidene compounds as cannabinoid receptor ligands |
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. |
CN101711253A (zh) * | 2007-05-18 | 2010-05-19 | 雅培制药有限公司 | 用作大麻素受体配体的新化合物 |
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 |
EP2428507B1 (en) * | 2008-09-16 | 2015-10-21 | AbbVie Bahamas Ltd. | 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 |
WO2011009883A1 (en) | 2009-07-23 | 2011-01-27 | INSERM (Institut National de la Santé et de la Recherche Médicale) | 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 |
WO2011100359A1 (en) * | 2010-02-09 | 2011-08-18 | 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 |
AP2016009270A0 (en) * | 2013-11-28 | 2016-06-30 | Commw Scient Ind Res Org | Method of detecting plasmodium infection |
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)
Publication number | Priority date | Publication date | Assignee | Title |
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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 |
AU1095101A (en) * | 1999-10-18 | 2001-04-30 | University Of Connecticut, The | Cannabimimetic indole derivatives |
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2000
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2001
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- 2001-11-21 NZ NZ525609A patent/NZ525609A/en unknown
- 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 JP JP2002544405A patent/JP4264258B2/ja not_active Expired - Fee Related
- 2001-11-21 EP EP01997476A patent/EP1339679B1/fr not_active Expired - Lifetime
- 2001-11-21 EE EEP200300244A patent/EE200300244A/xx unknown
- 2001-11-21 CA CA002427444A patent/CA2427444A1/fr not_active Abandoned
- 2001-11-21 HU HU0400561A patent/HUP0400561A2/hu unknown
- 2001-11-21 DZ DZ013443A patent/DZ3443A1/fr active
- 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 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
- 2001-11-21 DK DK01997476T patent/DK1339679T3/da active
- 2001-11-21 IL IL15563401A patent/IL155634A0/xx unknown
- 2001-11-21 AR ARP010105425A patent/AR033594A1/es not_active Application Discontinuation
- 2001-11-21 WO PCT/FR2001/003665 patent/WO2002042269A1/fr not_active Application Discontinuation
- 2001-11-21 ES ES01997476T patent/ES2247201T3/es not_active Expired - Lifetime
- 2001-11-21 BR BR0115580-6A patent/BR0115580A/pt not_active IP Right Cessation
- 2001-11-21 US US10/416,617 patent/US6995184B2/en not_active Expired - Fee Related
- 2001-11-22 TW TW090128947A patent/TWI224592B/zh active
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2003
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- 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
- 2003-05-22 HR HR20030417A patent/HRP20030417A2/hr not_active Application Discontinuation
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