UA77280C2 - Thiazole derivatives having antagonist, agonist or partially agonist activity relative to cb1 - Google Patents

Thiazole derivatives having antagonist, agonist or partially agonist activity relative to cb1 Download PDF

Info

Publication number: UA77280C2
Authority: UA; Ukraine
Prior art keywords: group; unbranched; branched; alkyl; hydroxy
Prior art date: 2002-03-18

Application number

UA20041008458A

Other languages

English (en)

Ukrainian (uk)

Inventor

Cornelis G Kruse

Arnoldus G Y Gerremans

Andrew K Mccriri

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.)

2002-03-18

Filing date

2003-03-17

Publication date

2006-11-15

2003-03-17 Application filed filed Critical

2006-11-15 Publication of UA77280C2 publication Critical patent/UA77280C2/uk

Links

150000007979 thiazole derivatives Chemical class 0.000 title abstract description 7
239000000556 agonist Substances 0.000 title abstract description 6
239000005557 antagonist Substances 0.000 title abstract description 5
230000000694 effects Effects 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 38
229930003827 cannabinoid Natural products 0.000 claims abstract description 7
239000003557 cannabinoid Substances 0.000 claims abstract description 7
-1 trifluoromethylthio, nitro, amino Chemical group 0.000 claims description 36
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 27
125000001424 substituent group Chemical group 0.000 claims description 27
125000000623 heterocyclic group Chemical group 0.000 claims description 22
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 21
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 18
125000001153 fluoro group Chemical group F* 0.000 claims description 18
125000005842 heteroatom Chemical group 0.000 claims description 18
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
125000001544 thienyl group Chemical group 0.000 claims description 17
125000004076 pyridyl group Chemical group 0.000 claims description 16
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 14
208000035475 disorder Diseases 0.000 claims description 14
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 11
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 11
125000004429 atom Chemical group 0.000 claims description 11
125000002619 bicyclic group Chemical group 0.000 claims description 11
229910052731 fluorine Inorganic materials 0.000 claims description 11
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
125000002950 monocyclic group Chemical group 0.000 claims description 11
229910052757 nitrogen Inorganic materials 0.000 claims description 11
125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
229920006395 saturated elastomer Polymers 0.000 claims description 11
125000003545 alkoxy group Chemical group 0.000 claims description 10
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
229910052736 halogen Inorganic materials 0.000 claims description 10
150000002367 halogens Chemical class 0.000 claims description 10
125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 10
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 9
125000003118 aryl group Chemical group 0.000 claims description 9
239000000651 prodrug Chemical group 0.000 claims description 9
229940002612 prodrug Drugs 0.000 claims description 9
125000000714 pyrimidinyl group Chemical group 0.000 claims description 8
150000003839 salts Chemical class 0.000 claims description 8
125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 8
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
208000006011 Stroke Diseases 0.000 claims description 6
208000030886 Traumatic Brain injury Diseases 0.000 claims description 6
QMHAHUAQAJVBIW-UHFFFAOYSA-N [methyl(sulfamoyl)amino]methane Chemical compound CN(C)S(N)(=O)=O QMHAHUAQAJVBIW-UHFFFAOYSA-N 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
201000006417 multiple sclerosis Diseases 0.000 claims description 6
230000009529 traumatic brain injury Effects 0.000 claims description 6
206010029216 Nervousness Diseases 0.000 claims description 4
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229940065144 cannabinoids Drugs 0.000 claims description 4
201000010099 disease Diseases 0.000 claims description 4
239000008194 pharmaceutical composition Substances 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 4
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208000024827 Alzheimer disease Diseases 0.000 claims description 3
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206010012735 Diarrhoea Diseases 0.000 claims description 3
208000014094 Dystonic disease Diseases 0.000 claims description 3
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208000019454 Feeding and Eating disease Diseases 0.000 claims description 3
208000018522 Gastrointestinal disease Diseases 0.000 claims description 3
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208000003286 Protein-Energy Malnutrition Diseases 0.000 claims description 3
YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 claims description 3
208000028017 Psychotic disease Diseases 0.000 claims description 3
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208000000323 Tourette Syndrome Diseases 0.000 claims description 3
208000016620 Tourette disease Diseases 0.000 claims description 3
206010047700 Vomiting Diseases 0.000 claims description 3
201000007930 alcohol dependence Diseases 0.000 claims description 3
208000006673 asthma Diseases 0.000 claims description 3
201000011510 cancer Diseases 0.000 claims description 3
230000002490 cerebral effect Effects 0.000 claims description 3
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230000006735 deficit Effects 0.000 claims description 3
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206010013663 drug dependence Diseases 0.000 claims description 3
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206010015037 epilepsy Diseases 0.000 claims description 3
206010026820 marasmus Diseases 0.000 claims description 3
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208000011117 substance-related disease Diseases 0.000 claims description 3
201000002498 viral encephalitis Diseases 0.000 claims description 3
230000008673 vomiting Effects 0.000 claims description 3
206010012305 Demyelination Diseases 0.000 claims description 2
125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
125000005119 alkyl cycloalkyl group Chemical group 0.000 claims 6
239000001257 hydrogen Substances 0.000 claims 6
229910052739 hydrogen Inorganic materials 0.000 claims 6
125000005843 halogen group Chemical group 0.000 claims 3
235000013599 spices Nutrition 0.000 claims 2
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
208000019901 Anxiety disease Diseases 0.000 claims 1
206010015137 Eructation Diseases 0.000 claims 1
101100209990 Rattus norvegicus Slc18a2 gene Proteins 0.000 claims 1
239000004480 active ingredient Substances 0.000 claims 1
230000036506 anxiety Effects 0.000 claims 1
208000027687 belching Diseases 0.000 claims 1
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
210000003169 central nervous system Anatomy 0.000 claims 1
229910052801 chlorine Inorganic materials 0.000 claims 1
125000001309 chloro group Chemical group Cl* 0.000 claims 1
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
125000001624 naphthyl group Chemical group 0.000 claims 1
238000012876 topography Methods 0.000 claims 1
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
239000004031 partial agonist Substances 0.000 abstract description 4
230000003389 potentiating effect Effects 0.000 abstract description 3
102000009132 CB1 Cannabinoid Receptor Human genes 0.000 abstract 1
108010073366 CB1 Cannabinoid Receptor Proteins 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
238000002844 melting Methods 0.000 description 28
230000008018 melting Effects 0.000 description 28
239000000243 solution Substances 0.000 description 25
QWEWLLNSJDTOKH-UHFFFAOYSA-N 1,3-thiazole-2-carboxamide Chemical compound NC(=O)C1=NC=CS1 QWEWLLNSJDTOKH-UHFFFAOYSA-N 0.000 description 21
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
239000000203 mixture Substances 0.000 description 21
238000005160 1H NMR spectroscopy Methods 0.000 description 15
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
102000018208 Cannabinoid Receptor Human genes 0.000 description 9
108050007331 Cannabinoid receptor Proteins 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
239000003921 oil Substances 0.000 description 8
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238000006243 chemical reaction Methods 0.000 description 7
239000002244 precipitate Substances 0.000 description 7
238000010992 reflux Methods 0.000 description 7
238000003756 stirring Methods 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
UMURHZMZTARHHZ-UHFFFAOYSA-N ethyl 5-(4-chlorophenyl)-4-(2,4-dichlorophenyl)-1,3-thiazole-2-carboxylate Chemical compound S1C(C(=O)OCC)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1C1=CC=C(Cl)C=C1 UMURHZMZTARHHZ-UHFFFAOYSA-N 0.000 description 5
239000007787 solid Substances 0.000 description 5
ZEWJUZAXIOVKHV-UHFFFAOYSA-N 5-(4-bromophenyl)-4-(2,4-dichlorophenyl)-1,3-thiazole-2-carboxylic acid Chemical compound S1C(C(=O)O)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1C1=CC=C(Br)C=C1 ZEWJUZAXIOVKHV-UHFFFAOYSA-N 0.000 description 4
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 4
230000001270 agonistic effect Effects 0.000 description 4
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XQXUWZVNQWBASZ-UHFFFAOYSA-N 2-(4-chlorophenyl)-1-(2,4-dichlorophenyl)ethanone Chemical compound C1=CC(Cl)=CC=C1CC(=O)C1=CC=C(Cl)C=C1Cl XQXUWZVNQWBASZ-UHFFFAOYSA-N 0.000 description 3
ZPORBADPRNAGJD-UHFFFAOYSA-N 5-(4-chlorophenyl)-4-(2,4-dichlorophenyl)-1,3-thiazole-2-carboxylic acid Chemical compound S1C(C(=O)O)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1C1=CC=C(Cl)C=C1 ZPORBADPRNAGJD-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
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UA20041008458A 2002-03-18 2003-03-17 Thiazole derivatives having antagonist, agonist or partially agonist activity relative to cb1 UA77280C2 (en)

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Application Number	Priority Date	Filing Date	Title
EP02076481		2002-03-18
PCT/EP2003/050063 WO2003078413A1 (en)	2002-03-18	2003-03-17	Thiazole derivatives having cb1-antagonistic, agonistic or partial agonistic activity

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UA77280C2 true UA77280C2 (en)	2006-11-15

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EP (1)	EP1492779A1 (pl)
JP (2)	JP2005529855A (pl)
KR (1)	KR100942672B1 (pl)
CN (2)	CN1592744A (pl)
AR (1)	AR038966A1 (pl)
AU (1)	AU2003219164B2 (pl)
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US7247628B2 (en)	2002-12-12	2007-07-24	Pfizer, Inc.	Cannabinoid receptor ligands and uses thereof
GB0230087D0 (en) *	2002-12-24	2003-01-29	Astrazeneca Ab	Therapeutic agents
US7329658B2 (en)	2003-02-06	2008-02-12	Pfizer Inc	Cannabinoid receptor ligands and uses thereof
GB0302672D0 (en) *	2003-02-06	2003-03-12	Astrazeneca Ab	Pharmaceutical formulations
US7176210B2 (en)	2003-02-10	2007-02-13	Pfizer Inc.	Cannabinoid receptor ligands and uses thereof
US7268133B2 (en)	2003-04-23	2007-09-11	Pfizer, Inc. Patent Department	Cannabinoid receptor ligands and uses thereof
US7145012B2 (en)	2003-04-23	2006-12-05	Pfizer Inc.	Cannabinoid receptor ligands and uses thereof
US7141669B2 (en)	2003-04-23	2006-11-28	Pfizer Inc.	Cannabiniod receptor ligands and uses thereof
US7232823B2 (en)	2003-06-09	2007-06-19	Pfizer, Inc.	Cannabinoid receptor ligands and uses thereof
US7292333B2 (en) *	2003-06-24	2007-11-06	Corning Incorporated	Optical interrogation system and method for 2-D sensor arrays
SA04250288B1 (ar) *	2003-09-19	2008-07-19	سولفاي فارماسوتيكالز بي . في	مشتقات ثيازول thiazole كمعدلات لمستقبل المكونات الكيميائية للقنب cannabinoid
FR2860792B1 (fr) *	2003-10-10	2006-02-24	Sanofi Synthelabo	Derives de thiophene-2-carboxamide, leur preparation et leur application en therapeutique
CA2543338A1 (en) *	2003-10-24	2005-05-06	Solvay Pharmaceuticals Gmbh	Novel medical uses of compounds showing cb1-antagonistic activity and combination treatment involving said compounds
CN100509808C (zh) *	2003-12-08	2009-07-08	霍夫曼-拉罗奇有限公司	新型噻唑衍生物
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- 2003-03-13 AR ARP030100879A patent/AR038966A1/es unknown
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- 2003-03-17 KR KR1020047014698A patent/KR100942672B1/ko not_active Expired - Fee Related
- 2003-03-17 HR HR20040274A patent/HRP20040274A2/hr not_active Application Discontinuation
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- 2003-03-17 CN CNA038015587A patent/CN1592744A/zh active Pending
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Also Published As

Publication number	Publication date
IL160945A (en)	2010-02-17
NO329617B1 (no)	2010-11-22
US7342032B2 (en)	2008-03-11
CN1592744A (zh)	2005-03-09
AU2003219164A1 (en)	2003-09-29
AR038966A1 (es)	2005-02-02
CN101550114A (zh)	2009-10-07
CA2462692C (en)	2010-11-09
JP2011105734A (ja)	2011-06-02
PL371429A1 (pl)	2005-06-13
HRP20040274A2 (en)	2005-04-30
NO20044319L (no)	2004-10-12
AU2003219164B2 (en)	2008-07-17
RU2301804C2 (ru)	2007-06-27
US20040266841A1 (en)	2004-12-30
EP1492779A1 (en)	2005-01-05
IL160945A0 (en)	2004-08-31
ZA200404742B (en)	2005-08-29
MXPA04004741A (es)	2004-08-02
KR100942672B1 (ko)	2010-02-17
BR0306150A (pt)	2004-10-19
RU2004114263A (ru)	2005-09-10
JP2005529855A (ja)	2005-10-06
KR20040106297A (ko)	2004-12-17
WO2003078413A1 (en)	2003-09-25
CA2462692A1 (en)	2003-09-25

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