JP2004505006A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2004505006A5 JP2004505006A5 JP2001534374A JP2001534374A JP2004505006A5 JP 2004505006 A5 JP2004505006 A5 JP 2004505006A5 JP 2001534374 A JP2001534374 A JP 2001534374A JP 2001534374 A JP2001534374 A JP 2001534374A JP 2004505006 A5 JP2004505006 A5 JP 2004505006A5
- Authority
- JP
- Japan
- Prior art keywords
- hydrogen
- straight
- alkyl
- branched chain
- chain alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 125000000217 alkyl group Chemical group 0.000 description 92
- 229910052739 hydrogen Inorganic materials 0.000 description 61
- 239000001257 hydrogen Substances 0.000 description 61
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 48
- 230000000694 effects Effects 0.000 description 40
- 150000001875 compounds Chemical class 0.000 description 38
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- 102100007437 CNR2 Human genes 0.000 description 28
- 230000002093 peripheral Effects 0.000 description 28
- 102000009135 CB2 Cannabinoid Receptor Human genes 0.000 description 26
- 108010073376 CB2 Cannabinoid Receptor Proteins 0.000 description 26
- 208000002193 Pain Diseases 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- 230000036407 pain Effects 0.000 description 24
- 239000000243 solution Substances 0.000 description 24
- -1 1,1-dimethyl-heptyl Chemical group 0.000 description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- 230000003042 antagnostic Effects 0.000 description 20
- 239000005557 antagonist Substances 0.000 description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 20
- 201000010099 disease Diseases 0.000 description 18
- 241000700159 Rattus Species 0.000 description 17
- JZCPYUJPEARBJL-UHFFFAOYSA-N Rimonabant Chemical compound CC=1C(C(=O)NN2CCCCC2)=NN(C=2C(=CC(Cl)=CC=2)Cl)C=1C1=CC=C(Cl)C=C1 JZCPYUJPEARBJL-UHFFFAOYSA-N 0.000 description 17
- 239000000556 agonist Substances 0.000 description 17
- 241001465754 Metazoa Species 0.000 description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 16
- 230000002194 synthesizing Effects 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 230000015572 biosynthetic process Effects 0.000 description 15
- 239000008194 pharmaceutical composition Substances 0.000 description 15
- 238000003786 synthesis reaction Methods 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 230000036772 blood pressure Effects 0.000 description 14
- 238000002347 injection Methods 0.000 description 14
- 239000007924 injection Substances 0.000 description 14
- 150000002431 hydrogen Chemical class 0.000 description 13
- 239000000463 material Substances 0.000 description 13
- 229940114079 Arachidonic Acid Drugs 0.000 description 12
- YZXBAPSDXZZRGB-DOFZRALJSA-N Arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 230000003110 anti-inflammatory Effects 0.000 description 12
- 235000021342 arachidonic acid Nutrition 0.000 description 12
- 230000002149 cannabinoid Effects 0.000 description 12
- 229930003827 cannabinoid Natural products 0.000 description 12
- 239000003557 cannabinoid Substances 0.000 description 12
- 230000001404 mediated Effects 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- 230000002829 reduced Effects 0.000 description 11
- CGIGDMFJXJATDK-UHFFFAOYSA-N Indometacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 10
- 238000004166 bioassay Methods 0.000 description 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 10
- 229910052736 halogen Inorganic materials 0.000 description 10
- 150000002367 halogens Chemical group 0.000 description 10
- 239000010410 layer Substances 0.000 description 10
- 239000012044 organic layer Substances 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- 239000011734 sodium Substances 0.000 description 10
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 206010003816 Autoimmune disease Diseases 0.000 description 9
- 210000003169 Central Nervous System Anatomy 0.000 description 9
- 239000004480 active ingredient Substances 0.000 description 9
- 229940065144 cannabinoids Drugs 0.000 description 9
- 230000001939 inductive effect Effects 0.000 description 9
- 239000011780 sodium chloride Substances 0.000 description 9
- 230000002522 swelling Effects 0.000 description 9
- LGEQQWMQCRIYKG-DOFZRALJSA-N Anandamide Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NCCO LGEQQWMQCRIYKG-DOFZRALJSA-N 0.000 description 8
- 102000009132 CB1 Cannabinoid Receptor Human genes 0.000 description 8
- 108010073366 CB1 Cannabinoid Receptor Proteins 0.000 description 8
- 206010021972 Inflammatory bowel disease Diseases 0.000 description 8
- 206010028980 Neoplasm Diseases 0.000 description 8
- 241000452413 Sabra Species 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 239000003085 diluting agent Substances 0.000 description 8
- 201000002491 encephalomyelitis Diseases 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 230000000506 psychotropic Effects 0.000 description 8
- 102000005962 receptors Human genes 0.000 description 8
- 108020003175 receptors Proteins 0.000 description 8
- FYZUENZXIZCLAZ-UHFFFAOYSA-N 2-methylhept-2-enoic acid Chemical compound CCCCC=C(C)C(O)=O FYZUENZXIZCLAZ-UHFFFAOYSA-N 0.000 description 7
- 206010071155 Autoimmune arthritis Diseases 0.000 description 7
- 210000001072 Colon Anatomy 0.000 description 7
- 208000008665 Gastrointestinal Disease Diseases 0.000 description 7
- 206010020772 Hypertension Diseases 0.000 description 7
- 206010061218 Inflammation Diseases 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
- 239000000969 carrier Substances 0.000 description 7
- 239000003814 drug Substances 0.000 description 7
- 230000004054 inflammatory process Effects 0.000 description 7
- RCRCTBLIHCHWDZ-UHFFFAOYSA-N 5Z,8Z,11Z,14Z-eicosatetraenoic acid, 2-glyceryl ester Chemical compound CCCCCC=CCC=CCC=CCC=CCCCC(=O)OC(CO)CO RCRCTBLIHCHWDZ-UHFFFAOYSA-N 0.000 description 6
- 102000018208 Cannabinoid receptor family Human genes 0.000 description 6
- 108050007331 Cannabinoid receptor family Proteins 0.000 description 6
- 206010012735 Diarrhoea Diseases 0.000 description 6
- 210000003414 Extremities Anatomy 0.000 description 6
- 210000003141 Lower Extremity Anatomy 0.000 description 6
- 230000000202 analgesic Effects 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 125000004432 carbon atoms Chemical group C* 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000006184 cosolvent Substances 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- 230000004899 motility Effects 0.000 description 6
- 230000001575 pathological Effects 0.000 description 6
- 230000002265 prevention Effects 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 210000004369 Blood Anatomy 0.000 description 5
- 102000008186 Collagen Human genes 0.000 description 5
- 108010035532 Collagen Proteins 0.000 description 5
- 229960000905 Indomethacin Drugs 0.000 description 5
- 229950010765 Pivalate Drugs 0.000 description 5
- IUGYQRQAERSCNH-UHFFFAOYSA-N Pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 5
- 230000000240 adjuvant Effects 0.000 description 5
- 239000002671 adjuvant Substances 0.000 description 5
- 230000027455 binding Effects 0.000 description 5
- 239000008280 blood Substances 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- 229960005188 collagen Drugs 0.000 description 5
- 229920001436 collagen Polymers 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 125000000623 heterocyclic group Chemical group 0.000 description 5
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 description 5
- 230000000968 intestinal Effects 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- 239000001184 potassium carbonate Substances 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 206010014025 Ear swelling Diseases 0.000 description 4
- 206010018987 Haemorrhage Diseases 0.000 description 4
- 229960003015 Rimonabant Drugs 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 230000000740 bleeding Effects 0.000 description 4
- 231100000319 bleeding Toxicity 0.000 description 4
- 238000001647 drug administration Methods 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 238000003818 flash chromatography Methods 0.000 description 4
- 230000003053 immunization Effects 0.000 description 4
- 238000002649 immunization Methods 0.000 description 4
- HPQVWDOOUQVBTO-UHFFFAOYSA-N lithium aluminium hydride Substances [Li+].[Al-] HPQVWDOOUQVBTO-UHFFFAOYSA-N 0.000 description 4
- OCZDCIYGECBNKL-UHFFFAOYSA-N lithium;alumanuide Chemical compound [Li+].[AlH4-] OCZDCIYGECBNKL-UHFFFAOYSA-N 0.000 description 4
- 239000000693 micelle Substances 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 102000004169 proteins and genes Human genes 0.000 description 4
- 108090000623 proteins and genes Proteins 0.000 description 4
- 239000002464 receptor antagonist Substances 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 210000001519 tissues Anatomy 0.000 description 4
- CYQFCXCEBYINGO-ZYMOGRSISA-N (6aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-ol Chemical compound C1=C(C)CC[C@H]2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3C21 CYQFCXCEBYINGO-ZYMOGRSISA-N 0.000 description 3
- 210000003038 Endothelium Anatomy 0.000 description 3
- 206010018338 Glioma Diseases 0.000 description 3
- 208000001953 Hypotension Diseases 0.000 description 3
- 206010033799 Paralysis Diseases 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M Potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 206010068760 Ulcers Diseases 0.000 description 3
- 230000004913 activation Effects 0.000 description 3
- 238000000540 analysis of variance Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- CYQFCXCEBYINGO-IAGOWNOFSA-N delta1-THC Chemical compound C1=C(C)CC[C@H]2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3[C@@H]21 CYQFCXCEBYINGO-IAGOWNOFSA-N 0.000 description 3
- 201000008286 diarrhea Diseases 0.000 description 3
- DCOPUUMXTXDBNB-UHFFFAOYSA-N diclofenac Chemical compound OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl DCOPUUMXTXDBNB-UHFFFAOYSA-N 0.000 description 3
- 229960001259 diclofenac Drugs 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 230000002496 gastric Effects 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 238000004896 high resolution mass spectrometry Methods 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 231100000486 side effect Toxicity 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 231100000397 ulcer Toxicity 0.000 description 3
- 230000024883 vasodilation Effects 0.000 description 3
- GRWFGVWFFZKLTI-UHFFFAOYSA-N (+-)-2-pinene Chemical class CC1=CCC2C(C)(C)C1C2 GRWFGVWFFZKLTI-UHFFFAOYSA-N 0.000 description 2
- MONMFXREYOKQTI-UHFFFAOYSA-M 2-bromopropanoate Chemical compound CC(Br)C([O-])=O MONMFXREYOKQTI-UHFFFAOYSA-M 0.000 description 2
- 206010003246 Arthritis Diseases 0.000 description 2
- 208000003174 Brain Neoplasms Diseases 0.000 description 2
- MSNZUSRESABQTI-UHFFFAOYSA-N C1C(C)=C(C2(C)C)CC2C1C1=CC=CC=C1 Chemical class C1C(C)=C(C2(C)C)CC2C1C1=CC=CC=C1 MSNZUSRESABQTI-UHFFFAOYSA-N 0.000 description 2
- 241000700199 Cavia porcellus Species 0.000 description 2
- 208000000999 Encephalomyelitis, Autoimmune, Experimental Diseases 0.000 description 2
- 210000001035 Gastrointestinal Tract Anatomy 0.000 description 2
- 206010020565 Hyperaemia Diseases 0.000 description 2
- 206010021113 Hypothermia Diseases 0.000 description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N Imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
- 210000002540 Macrophages Anatomy 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N Methyl iodide Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 102000015528 Myelin Basic Protein Human genes 0.000 description 2
- 108010025255 Myelin Basic Protein Proteins 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- 150000001200 N-acyl ethanolamides Chemical class 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 206010030113 Oedema Diseases 0.000 description 2
- 208000005141 Otitis Diseases 0.000 description 2
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N Pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 2
- 229960001412 Pentobarbital Drugs 0.000 description 2
- 210000003491 Skin Anatomy 0.000 description 2
- FPGGTKZVZWFYPV-UHFFFAOYSA-M Tetra-n-butylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 230000036592 analgesia Effects 0.000 description 2
- 230000003502 anti-nociceptive Effects 0.000 description 2
- 210000000436 anus Anatomy 0.000 description 2
- 230000001363 autoimmune Effects 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 230000004531 blood pressure lowering effect Effects 0.000 description 2
- 239000003556 cannabinoid 2 receptor agonist Substances 0.000 description 2
- 230000000271 cardiovascular Effects 0.000 description 2
- 210000004027 cells Anatomy 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 230000002860 competitive Effects 0.000 description 2
- 229960004242 dronabinol Drugs 0.000 description 2
- 229940079593 drugs Drugs 0.000 description 2
- 230000000534 elicitor Effects 0.000 description 2
- 239000002621 endocannabinoid Substances 0.000 description 2
- 239000002158 endotoxin Substances 0.000 description 2
- 230000003628 erosive Effects 0.000 description 2
- 125000001033 ether group Chemical group 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 230000036543 hypotension Effects 0.000 description 2
- 230000002631 hypothermal Effects 0.000 description 2
- 230000002757 inflammatory Effects 0.000 description 2
- 239000002563 ionic surfactant Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000006011 modification reaction Methods 0.000 description 2
- 201000006417 multiple sclerosis Diseases 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- 201000008125 pain agnosia Diseases 0.000 description 2
- 201000008175 pain disease Diseases 0.000 description 2
- HXYVTAGFYLMHSO-UHFFFAOYSA-N palmitoyl ethanolamide Chemical compound CCCCCCCCCCCCCCCC(=O)NCCO HXYVTAGFYLMHSO-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 230000001629 suppression Effects 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N t-BuOH Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 230000001225 therapeutic Effects 0.000 description 2
- 230000000007 visual effect Effects 0.000 description 2
- 230000004580 weight loss Effects 0.000 description 2
- PDVFSPNIEOYOQL-UHFFFAOYSA-N (4-methylphenyl)sulfonyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OS(=O)(=O)C1=CC=C(C)C=C1 PDVFSPNIEOYOQL-UHFFFAOYSA-N 0.000 description 1
- JLPULHDHAOZNQI-ZTIMHPMXSA-N 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC JLPULHDHAOZNQI-ZTIMHPMXSA-N 0.000 description 1
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-Methyl-2-butene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 1
- KWVPFECTOKLOBL-KTKRTIGZSA-N 2-[(Z)-octadec-9-enoxy]ethanol Chemical compound CCCCCCCC\C=C/CCCCCCCCOCCO KWVPFECTOKLOBL-KTKRTIGZSA-N 0.000 description 1
- GWBGUJWRDDDVBI-UHFFFAOYSA-N 5-(2-methyloctan-2-yl)benzene-1,3-diol Chemical compound CCCCCCC(C)(C)C1=CC(O)=CC(O)=C1 GWBGUJWRDDDVBI-UHFFFAOYSA-N 0.000 description 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N 5-(7-(4-(4,5-DIHYDRO-2-OXAZOLYL)PHENOXY)HEPTYL)-3-METHYL ISOXAZOLE Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 1
- 229940035676 ANALGESICS Drugs 0.000 description 1
- 206010000565 Acquired immunodeficiency syndrome Diseases 0.000 description 1
- 244000144725 Amygdalus communis Species 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- 210000000709 Aorta Anatomy 0.000 description 1
- 206010059512 Apoptosis Diseases 0.000 description 1
- 210000003719 B-Lymphocytes Anatomy 0.000 description 1
- 230000035639 Blood Levels Effects 0.000 description 1
- 210000001772 Blood Platelets Anatomy 0.000 description 1
- 210000004556 Brain Anatomy 0.000 description 1
- 229960004484 CARBACHOL Drugs 0.000 description 1
- CISSBSWCHLNHCN-UHFFFAOYSA-N CC1=CC(=C(C(=C1O)CCCCCCC)O)C Chemical compound CC1=CC(=C(C(=C1O)CCCCCCC)O)C CISSBSWCHLNHCN-UHFFFAOYSA-N 0.000 description 1
- XCGGBYOSVRKUKW-DKADZPKRSA-N CCCCCCC(C)(C)c1cc(OCC(C)=O)c([C@]2(C34C5C3C24)C=C5C(O)=O)c(OCC(C)=O)c1 Chemical compound CCCCCCC(C)(C)c1cc(OCC(C)=O)c([C@]2(C34C5C3C24)C=C5C(O)=O)c(OCC(C)=O)c1 XCGGBYOSVRKUKW-DKADZPKRSA-N 0.000 description 1
- YQEZLKZALYSWHR-UHFFFAOYSA-N Calypsol Chemical compound C=1C=CC=C(Cl)C=1C1(NC)CCCCC1=O YQEZLKZALYSWHR-UHFFFAOYSA-N 0.000 description 1
- 241000218236 Cannabis Species 0.000 description 1
- 240000000218 Cannabis sativa Species 0.000 description 1
- 235000008697 Cannabis sativa Nutrition 0.000 description 1
- AIXAANGOTKPUOY-UHFFFAOYSA-N Carbachol Chemical compound [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 description 1
- BULLHNJGPPOUOX-UHFFFAOYSA-N Chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 description 1
- LMYWWPCAXXPJFF-UHFFFAOYSA-P Cornforth reagent Chemical compound C1=CC=[NH+]C=C1.C1=CC=[NH+]C=C1.[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O LMYWWPCAXXPJFF-UHFFFAOYSA-P 0.000 description 1
- 102000004127 Cytokines Human genes 0.000 description 1
- 108090000695 Cytokines Proteins 0.000 description 1
- 206010061818 Disease progression Diseases 0.000 description 1
- CYQFCXCEBYINGO-DLBZAZTESA-N Dronabinol Natural products C1=C(C)CC[C@H]2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3[C@H]21 CYQFCXCEBYINGO-DLBZAZTESA-N 0.000 description 1
- 206010014599 Encephalitis Diseases 0.000 description 1
- 206010015150 Erythema Diseases 0.000 description 1
- 210000001105 Femoral Artery Anatomy 0.000 description 1
- 206010019468 Hemiplegia Diseases 0.000 description 1
- ZFGMDIBRIDKWMY-PASTXAENSA-N Heparin Chemical compound CC(O)=N[C@@H]1[C@@H](O)[C@H](O)[C@@H](COS(O)(=O)=O)O[C@@H]1O[C@@H]1[C@@H](C(O)=O)O[C@@H](O[C@H]2[C@@H]([C@@H](OS(O)(=O)=O)[C@@H](O[C@@H]3[C@@H](OC(O)[C@H](OS(O)(=O)=O)[C@H]3O)C(O)=O)O[C@@H]2O)CS(O)(=O)=O)[C@H](O)[C@H]1O ZFGMDIBRIDKWMY-PASTXAENSA-N 0.000 description 1
- 229960002897 Heparin Drugs 0.000 description 1
- 206010022114 Injury Diseases 0.000 description 1
- 210000000936 Intestines Anatomy 0.000 description 1
- 210000004731 Jugular Veins Anatomy 0.000 description 1
- 229940067606 Lecithin Drugs 0.000 description 1
- 238000000585 Mann–Whitney U test Methods 0.000 description 1
- 210000002464 Muscle, Smooth, Vascular Anatomy 0.000 description 1
- 210000000578 Peripheral Nerves Anatomy 0.000 description 1
- 210000001428 Peripheral Nervous System Anatomy 0.000 description 1
- DDBREPKUVSBGFI-UHFFFAOYSA-N Phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 1
- 229960002695 Phenobarbital Drugs 0.000 description 1
- 239000004698 Polyethylene (PE) Substances 0.000 description 1
- 240000000037 Prosopis spicigera Species 0.000 description 1
- 235000006629 Prosopis spicigera Nutrition 0.000 description 1
- 210000000664 Rectum Anatomy 0.000 description 1
- 241000283984 Rodentia Species 0.000 description 1
- 229940069575 Rompun Drugs 0.000 description 1
- 210000002265 Sensory Receptor Cells Anatomy 0.000 description 1
- 210000000278 Spinal Cord Anatomy 0.000 description 1
- 238000003639 Student–Newman–Keuls (SNK) method Methods 0.000 description 1
- 210000003568 Synaptosomes Anatomy 0.000 description 1
- 229940033529 Tetrahydrocannabinol Drugs 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- HQVHOQAKMCMIIM-UHFFFAOYSA-N WIN 55,212-2 Chemical compound C=12N3C(C)=C(C(=O)C=4C5=CC=CC=C5C=CC=4)C2=CC=CC=1OCC3CN1CCOCC1 HQVHOQAKMCMIIM-UHFFFAOYSA-N 0.000 description 1
- BPICBUSOMSTKRF-UHFFFAOYSA-N Xylazine Chemical compound CC1=CC=CC(C)=C1NC1=NCCCS1 BPICBUSOMSTKRF-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 102000034433 acetylcholine receptors Human genes 0.000 description 1
- 108020000715 acetylcholine receptors Proteins 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 230000001270 agonistic Effects 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 230000000111 anti-oxidant Effects 0.000 description 1
- 239000000427 antigen Substances 0.000 description 1
- 102000038129 antigens Human genes 0.000 description 1
- 108091007172 antigens Proteins 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000006907 apoptotic process Effects 0.000 description 1
- 230000036528 appetite Effects 0.000 description 1
- 235000019789 appetite Nutrition 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 201000009596 autoimmune hypersensitivity disease Diseases 0.000 description 1
- 238000009227 behaviour therapy Methods 0.000 description 1
- 230000003542 behavioural Effects 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000036760 body temperature Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000003555 cannabinoid 1 receptor antagonist Substances 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000003197 catalytic Effects 0.000 description 1
- LKYXEULZVGJVTG-UHFFFAOYSA-N chloromethane Chemical compound Cl[CH] LKYXEULZVGJVTG-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 230000034994 death Effects 0.000 description 1
- 230000013872 defecation Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000003511 endothelial Effects 0.000 description 1
- 230000002708 enhancing Effects 0.000 description 1
- 230000001586 eradicative Effects 0.000 description 1
- 231100000321 erythema Toxicity 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 230000005021 gait Effects 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- 230000005176 gastrointestinal motility Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000005534 hematocrit Methods 0.000 description 1
- 230000002008 hemorrhagic Effects 0.000 description 1
- 229920000669 heparin Polymers 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001077 hypotensive Effects 0.000 description 1
- 230000036737 immune function Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 229960003299 ketamine Drugs 0.000 description 1
- 230000002147 killing Effects 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 230000003902 lesions Effects 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 230000000670 limiting Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000003211 malignant Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 230000000051 modifying Effects 0.000 description 1
- 230000037023 motor activity Effects 0.000 description 1
- 230000000926 neurological Effects 0.000 description 1
- 230000000324 neuroprotective Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229940021182 non-steroidal anti-inflammatory drugs Drugs 0.000 description 1
- 238000001543 one-way ANOVA Methods 0.000 description 1
- 210000000056 organs Anatomy 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 238000010149 post-hoc-test Methods 0.000 description 1
- 230000003389 potentiating Effects 0.000 description 1
- 238000000159 protein binding assay Methods 0.000 description 1
- 239000000018 receptor agonist Substances 0.000 description 1
- 238000001525 receptor binding assay Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 210000001044 sensory neuron Anatomy 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- BZKBCQXYZZXSCO-UHFFFAOYSA-N sodium hydride Inorganic materials [H-].[Na+] BZKBCQXYZZXSCO-UHFFFAOYSA-N 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000002269 spontaneous Effects 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 230000000699 topical Effects 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 201000008827 tuberculosis Diseases 0.000 description 1
- 210000004881 tumor cells Anatomy 0.000 description 1
- 238000007492 two-way ANOVA Methods 0.000 description 1
- 230000000304 vasodilatating Effects 0.000 description 1
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IL132661A IL132661A (en) | 1999-10-31 | 1999-10-31 | Agonists specific for peripheral cannabinoid receptors |
PCT/US2000/029903 WO2001032169A1 (en) | 1999-10-31 | 2000-10-30 | Agonists specific for the peripheral cannabinoid receptor |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2004505006A JP2004505006A (ja) | 2004-02-19 |
JP2004505006A5 true JP2004505006A5 (US06903137-20050607-C00013.png) | 2006-12-07 |
JP4231906B2 JP4231906B2 (ja) | 2009-03-04 |
Family
ID=11073405
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2001534374A Expired - Fee Related JP4231906B2 (ja) | 1999-10-31 | 2000-10-30 | 末梢カンナビノイド受容体に特異的なアゴニスト |
Country Status (13)
Families Citing this family (45)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6342611B1 (en) * | 1997-10-10 | 2002-01-29 | Cytovia, Inc. | Fluorogenic or fluorescent reporter molecules and their applications for whole-cell fluorescence screening assays for capsases and other enzymes and the use thereof |
DE69910373T2 (de) | 1998-05-04 | 2004-04-01 | The University Of Connecticut, Farmington | Analgetische und immunomodulierende cannabinoiden |
US7897598B2 (en) * | 1998-06-09 | 2011-03-01 | Alexandros Makriyannis | Inhibitors of the anandamide transporter |
US7589220B2 (en) * | 1998-06-09 | 2009-09-15 | University Of Connecticut | Inhibitors of the anandamide transporter |
US7276613B1 (en) | 1998-11-24 | 2007-10-02 | University Of Connecticut | Retro-anandamides, high affinity and stability cannabinoid receptor ligands |
US7161016B1 (en) | 1998-11-24 | 2007-01-09 | University Of Connecticut | Cannabimimetic lipid amides as useful medications |
US8084467B2 (en) * | 1999-10-18 | 2011-12-27 | University Of Connecticut | Pyrazole derivatives as cannabinoid receptor antagonists |
US6943266B1 (en) * | 1999-10-18 | 2005-09-13 | University Of Connecticut | Bicyclic cannabinoid agonists for the cannabinoid receptor |
JP2003511469A (ja) | 1999-10-18 | 2003-03-25 | ユニバーシティ オブ コネチカット | 抹消カンナビノイド受容体(cb2)選択的配位子 |
US6900236B1 (en) | 1999-10-18 | 2005-05-31 | University Of Connecticut | Cannabimimetic indole derivatives |
US7393842B2 (en) * | 2001-08-31 | 2008-07-01 | University Of Connecticut | Pyrazole analogs acting on cannabinoid receptors |
US7119108B1 (en) | 1999-10-18 | 2006-10-10 | University Of Connecticut | Pyrazole derivatives as cannabinoid receptor antagonists |
US7741365B2 (en) * | 1999-10-18 | 2010-06-22 | University Of Connecticut | Peripheral cannabinoid receptor (CB2) selective ligands |
IL132661A (en) * | 1999-10-31 | 2008-11-26 | Raphael Mechoulam | Agonists specific for peripheral cannabinoid receptors |
JP2004532185A (ja) * | 2001-01-26 | 2004-10-21 | ユニバーシティ オブ コネチカット | 新規なカンナビミメティックリガンド |
US7173027B2 (en) * | 2001-01-29 | 2007-02-06 | University Of Connecticut | Receptor selective cannabimimetic aminoalkylindoles |
WO2003005960A2 (en) * | 2001-07-13 | 2003-01-23 | University Of Connecticut | Novel bicyclic and tricyclic cannabinoids |
CA2464333C (en) | 2001-10-26 | 2011-07-26 | University Of Connecticut | Heteroindanes: a new class of potent cannabimimetic ligands |
TW200407110A (en) | 2001-11-23 | 2004-05-16 | Astrazeneca Ab | New use for the treatment of gastroesophageal reflux disease |
WO2003061699A1 (fr) * | 2001-12-27 | 2003-07-31 | Japan Tobacco, Inc. | Remedes pour affections allergiques |
EP1469842A4 (en) * | 2002-01-31 | 2006-04-26 | Pharmos Corp | BICYCLIC CB2 CANNABINOID RECEPTOR LIGANDS |
IL150302A (en) * | 2002-01-31 | 2008-07-08 | Naim Menashe | Bicyclic cb2 cannabinoid receptor ligands |
CA2496097A1 (en) | 2002-08-23 | 2004-03-04 | University Of Connecticut | Keto cannabinoids with therapeutic indications |
US20060172019A1 (en) * | 2003-03-07 | 2006-08-03 | Ralston Stuart H | Cannabinoid receptor inverse agonists and neutral antagonists as therapeutic agents for the treatment of bone disorders |
AR043633A1 (es) | 2003-03-20 | 2005-08-03 | Schering Corp | Ligandos de receptores de canabinoides |
US7169942B2 (en) * | 2003-05-20 | 2007-01-30 | University Of Tennessee Research Foundation | Cannabinoid derivatives, methods of making, and use thereof |
WO2005123053A2 (en) * | 2004-06-22 | 2005-12-29 | Pharmos Limited | Use of cb2 receptors agonists for the treatment of huntington’s disease |
TWI366460B (en) | 2005-06-16 | 2012-06-21 | Euro Celtique Sa | Cannabinoid active pharmaceutical ingredient for improved dosage forms |
US20070060638A1 (en) * | 2005-08-26 | 2007-03-15 | Olmstead Mary C | Methods and therapies for potentiating therapeutic activities of a cannabinoid receptor agonist via administration of a cannabinoid receptor antagonist |
CA2650566A1 (en) * | 2006-04-27 | 2007-11-08 | Solvay Pharmaceuticals Gmbh | Pharmaceutical compositions comprising cbx cannabinoid receptor modulators and potassium channel modulators |
US7763607B2 (en) | 2006-04-27 | 2010-07-27 | Solvay Pharmaceuticals Gmbh | Pharmaceutical compositions comprising CBx cannabinoid receptor modulators and potassium channel modulators |
WO2008001369A1 (en) * | 2006-06-27 | 2008-01-03 | Pharmos Corporation | Use of cb2 receptor agonists for promoting neurogenesis |
US9763894B2 (en) * | 2006-12-05 | 2017-09-19 | Virginia Commonwealth University | Inflammation therapy |
GB0702862D0 (en) * | 2007-02-14 | 2007-03-28 | Univ Aberdeen | Therapeutic compounds |
WO2008107879A1 (en) * | 2007-03-05 | 2008-09-12 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Novel cannabidiol derivatives and their use as anti-inflammatory agents |
JP2010540618A (ja) * | 2007-10-02 | 2010-12-24 | アリエル−ユニバーシティー リサーチ アンド デベロップメント カンパニー リミテッド | 幼児の成長および発達を増大するための内在性カンナビノイド |
US9193713B2 (en) | 2007-10-12 | 2015-11-24 | Abbvie Inc. | Compounds as cannabinoid receptor ligands |
WO2010041253A1 (en) | 2008-10-06 | 2010-04-15 | Yissum Research Development Company Of The Hebrew University Of Jerusalem, Ltd. | Compositions comprising cb receptor agonists, uses thereof and methods for their preparation |
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 |
ITMI20122221A1 (it) | 2012-12-21 | 2014-06-22 | C4T S C A R L | Nuovi composti del 2,3-diidro-4h-1,3-benzossazin-4-one, metodo per prepararli e forma farmaceutica che li comprende |
EP2986587B1 (en) | 2013-04-17 | 2023-11-22 | Sharon Anavi-Goffer | Cb2 receptor ligands for the treatment of psychiatric disorders |
EP2992880A1 (en) * | 2014-09-04 | 2016-03-09 | Fundació Institut de Recerca de l'Hospital de la Santa Creu l Sant Pau | Use of heme oxygenase 1 inducers and cannabinoid 2 receptor or delta-opioid receptor agonists in inflammatory pain |
US9585867B2 (en) | 2015-08-06 | 2017-03-07 | Charles Everett Ankner | Cannabinod formulation for the sedation of a human or animal |
US11612581B2 (en) | 2017-08-09 | 2023-03-28 | Cannibite Bvba | Cannabis and derivatives thereof for the treatment of pain and inflammation related with dental pulp and bone regeneration related to dental jaw bone defects |
WO2021080648A1 (en) * | 2019-10-25 | 2021-04-29 | Gelest Technologies, Inc. | Silicon-based cannabidiol derivatives and compositions thereof |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IL55274A (en) | 1978-08-02 | 1982-08-31 | Yissum Res Dev Co | 4-(2,6-dihydroxy-4-(dimethylheptyl)phenyl)substituted 2-pinen-10-ol and pinane derivatives,their preparation and pharmaceutical compositions comprising them |
US5434295A (en) | 1994-02-07 | 1995-07-18 | Yissum Research Development Company | Neuroprotective pharmaceutical compositions of 4-phenylpinene derivatives and certain novel 4-phenylpinene compounds |
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 |
IL132661A (en) * | 1999-10-31 | 2008-11-26 | Raphael Mechoulam | Agonists specific for peripheral cannabinoid receptors |
-
1999
- 1999-10-31 IL IL132661A patent/IL132661A/en not_active IP Right Cessation
-
2000
- 2000-10-30 WO PCT/US2000/029903 patent/WO2001032169A1/en active IP Right Grant
- 2000-10-30 JP JP2001534374A patent/JP4231906B2/ja not_active Expired - Fee Related
- 2000-10-30 US US09/698,071 patent/US6864291B1/en not_active Expired - Fee Related
- 2000-10-30 CA CA002385928A patent/CA2385928A1/en not_active Abandoned
- 2000-10-30 EP EP00974023A patent/EP1244440B1/en not_active Expired - Lifetime
- 2000-10-30 DE DE60017287T patent/DE60017287T2/de not_active Expired - Lifetime
- 2000-10-30 HU HU0203681A patent/HUP0203681A3/hu unknown
- 2000-10-30 KR KR1020027005566A patent/KR100770695B1/ko not_active IP Right Cessation
- 2000-10-30 NZ NZ518054A patent/NZ518054A/en unknown
- 2000-10-30 AU AU12458/01A patent/AU778149B2/en not_active Ceased
- 2000-10-30 AT AT00974023T patent/ATE286389T1/de not_active IP Right Cessation
-
2002
- 2002-03-18 ZA ZA200202181A patent/ZA200202181B/xx unknown
- 2002-03-20 IL IL148796A patent/IL148796A/en not_active IP Right Cessation
- 2002-04-26 US US10/133,153 patent/US6903137B2/en not_active Expired - Fee Related
-
2005
- 2005-01-27 US US11/043,089 patent/US7214716B2/en not_active Expired - Fee Related
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP4231906B2 (ja) | 末梢カンナビノイド受容体に特異的なアゴニスト | |
JP2004505006A5 (US06903137-20050607-C00013.png) | ||
CA2727561A1 (en) | Dihydrotetrabenanzine for the treatment of anxiety | |
JP3179501B2 (ja) | 抗炎症薬として有用なイオウ含有ジ−t−ブチルフェノール化合物 | |
WO1993007865A1 (en) | Di-tert-butylphenol compounds useful as anti-inflammatory agents | |
AU2003209616B2 (en) | Bicyclic CB2 cannabinoid receptor ligands | |
EP1469842A2 (en) | Bicyclic cb2 cannabinoid receptor ligands | |
AU2003209616A1 (en) | Bicyclic CB2 cannabinoid receptor ligands | |
KR20050044582A (ko) | 위식도 역류 질환의 치료를 위한 신규한 용도 | |
WO2005123053A2 (en) | Use of cb2 receptors agonists for the treatment of huntington’s disease | |
JP2006514084A (ja) | 1−(3−ヒドロキシ−4−メトキシフェニル)−4−メチル−5−エチル−7,8−ジメトキシ−5h−2,3−ベンゾジアゼピンの製薬組成物及びその用途 | |
Buchwald | Soft cannabinoid analogues as potential anti-glaucoma agents | |
KR870000284B1 (ko) | 2,5-디아릴 테트라하이드로티오펜 및 이의 동족체의 제조방법 | |
HUT74507A (en) | Use of di-tert-butylphenol compounds for producing pharmaceutical compositions having anti-inflammatory effect | |
FR2616326A1 (fr) | Compositions therapeutiques a base de nouveaux aminoacylates d'acetal du glycerol | |
JP2003252793A (ja) | 痔疾用医薬組成物 | |
AU1007599A (en) | Di-tert-butylphenol compounds useful as anti-inflammatory agents |