BRPI0607439A2 - compostos, composição farmacêutica, método de preparação de composições farmacêuticas, e, uso de um composto - Google Patents

compostos, composição farmacêutica, método de preparação de composições farmacêuticas, e, uso de um composto Download PDF

Info

Publication number: BRPI0607439A2
Authority: BR; Brazil
Prior art keywords: group; substituted; formula; substituents; alkyl
Prior art date: 2005-02-16

Application number

BRPI0607439-1A

Other languages

English (en)

Portuguese (pt)

Inventor

Josephus H M Lange

Vliet Bernard J Van

Herman H Stuivenberg

Original Assignee

Solvay Pharm Bv

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.)

2005-02-16

Filing date

2006-02-16

Publication date

2010-04-06

2006-02-16 Application filed by Solvay Pharm Bv filed Critical Solvay Pharm Bv

2010-04-06 Publication of BRPI0607439A2 publication Critical patent/BRPI0607439A2/pt

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 171
238000000034 method Methods 0.000 title claims abstract description 23
239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 15
238000003786 synthesis reaction Methods 0.000 claims abstract description 26
230000015572 biosynthetic process Effects 0.000 claims abstract description 25
102000009135 CB2 Cannabinoid Receptor Human genes 0.000 claims abstract description 20
108010073376 CB2 Cannabinoid Receptor Proteins 0.000 claims abstract description 20
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 15
238000002360 preparation method Methods 0.000 claims abstract description 8
208000035475 disorder Diseases 0.000 claims abstract description 5
-1 cyano, methylsulfonyl Chemical group 0.000 claims description 161
125000001424 substituent group Chemical group 0.000 claims description 139
125000001153 fluoro group Chemical group F* 0.000 claims description 71
125000001072 heteroaryl group Chemical group 0.000 claims description 68
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 62
125000002950 monocyclic group Chemical group 0.000 claims description 61
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 61
125000000217 alkyl group Chemical group 0.000 claims description 51
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 37
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 36
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 35
229910052731 fluorine Inorganic materials 0.000 claims description 32
125000000623 heterocyclic group Chemical group 0.000 claims description 31
125000004093 cyano group Chemical group *C#N 0.000 claims description 30
239000011737 fluorine Substances 0.000 claims description 30
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 28
125000002619 bicyclic group Chemical group 0.000 claims description 28
125000005843 halogen group Chemical group 0.000 claims description 27
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 27
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 26
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 25
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 24
229910052739 hydrogen Inorganic materials 0.000 claims description 21
239000001257 hydrogen Substances 0.000 claims description 21
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 19
125000003277 amino group Chemical group 0.000 claims description 19
229910052794 bromium Inorganic materials 0.000 claims description 19
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 19
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 18
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 17
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 17
229920006395 saturated elastomer Polymers 0.000 claims description 17
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 15
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 15
125000006592 (C2-C3) alkenyl group Chemical group 0.000 claims description 14
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 14
125000006526 (C1-C2) alkyl group Chemical group 0.000 claims description 13
125000006593 (C2-C3) alkynyl group Chemical group 0.000 claims description 12
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 12
125000002837 carbocyclic group Chemical group 0.000 claims description 12
LNQUWGZAZIOHMM-UHFFFAOYSA-N ethoxy-hydroxy-methoxy-lambda3-chlorane Chemical compound CCOCl(O)OC LNQUWGZAZIOHMM-UHFFFAOYSA-N 0.000 claims description 12
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 12
125000001624 naphthyl group Chemical group 0.000 claims description 12
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 12
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 11
150000001204 N-oxides Chemical class 0.000 claims description 10
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 10
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 9
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 9
229910052801 chlorine Inorganic materials 0.000 claims description 9
125000006125 ethylsulfonyl group Chemical group 0.000 claims description 9
125000004705 ethylthio group Chemical group C(C)S* 0.000 claims description 9
125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 9
125000003118 aryl group Chemical group 0.000 claims description 8
239000003814 drug Substances 0.000 claims description 8
229910052757 nitrogen Inorganic materials 0.000 claims description 8
125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
125000003725 azepanyl group Chemical group 0.000 claims description 7
125000001589 carboacyl group Chemical group 0.000 claims description 7
125000004404 heteroalkyl group Chemical group 0.000 claims description 7
125000002757 morpholinyl group Chemical group 0.000 claims description 7
125000003386 piperidinyl group Chemical group 0.000 claims description 7
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 7
125000006413 ring segment Chemical group 0.000 claims description 7
150000003839 salts Chemical class 0.000 claims description 7
125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 6
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 6
125000004429 atom Chemical group 0.000 claims description 6
125000005842 heteroatom Chemical group 0.000 claims description 6
125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 6
229910052760 oxygen Inorganic materials 0.000 claims description 6
102000005962 receptors Human genes 0.000 claims description 6
108020003175 receptors Proteins 0.000 claims description 6
239000000126 substance Substances 0.000 claims description 6
229910052717 sulfur Inorganic materials 0.000 claims description 6
125000004414 alkyl thio group Chemical group 0.000 claims description 5
125000000753 cycloalkyl group Chemical group 0.000 claims description 5
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 4
125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 claims description 4
125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 3
208000002193 Pain Diseases 0.000 claims description 3
125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 3
150000002367 halogens Chemical class 0.000 claims description 3
230000036407 pain Effects 0.000 claims description 3
125000001544 thienyl group Chemical group 0.000 claims description 3
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 2
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
208000023105 Huntington disease Diseases 0.000 claims description 2
206010020751 Hypersensitivity Diseases 0.000 claims description 2
206010028980 Neoplasm Diseases 0.000 claims description 2
229910003870 O—Li Inorganic materials 0.000 claims description 2
230000007815 allergy Effects 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
150000004677 hydrates Chemical class 0.000 claims description 2
208000026278 immune system disease Diseases 0.000 claims description 2
208000027866 inflammatory disease Diseases 0.000 claims description 2
239000004615 ingredient Substances 0.000 claims description 2
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
201000006417 multiple sclerosis Diseases 0.000 claims description 2
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 2
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
239000012453 solvate Substances 0.000 claims description 2
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
125000000304 alkynyl group Chemical group 0.000 claims 2
125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 1
125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims 1
AHOIGFLSEXUWNV-UHFFFAOYSA-N 6-methoxy-1,3-benzothiazole Chemical compound COC1=CC=C2N=CSC2=C1 AHOIGFLSEXUWNV-UHFFFAOYSA-N 0.000 claims 1
125000003342 alkenyl group Chemical group 0.000 claims 1
125000006267 biphenyl group Chemical group 0.000 claims 1
201000011510 cancer Diseases 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical class C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 abstract description 16
150000002460 imidazoles Chemical class 0.000 abstract description 8
229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 abstract description 6
239000000543 intermediate Substances 0.000 abstract description 5
102000018208 Cannabinoid Receptor Human genes 0.000 abstract description 3
108050007331 Cannabinoid receptor Proteins 0.000 abstract description 3
239000003520 cannabinoid receptor affecting agent Substances 0.000 abstract description 2
239000004480 active ingredient Substances 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 111
238000002844 melting Methods 0.000 description 77
230000008018 melting Effects 0.000 description 77
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 57
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 51
239000000243 solution Substances 0.000 description 45
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 38
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 26
238000005160 1H NMR spectroscopy Methods 0.000 description 24
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
239000000203 mixture Substances 0.000 description 24
238000004587 chromatography analysis Methods 0.000 description 23
238000006243 chemical reaction Methods 0.000 description 22
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 18
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 15
238000010168 coupling process Methods 0.000 description 15
230000014759 maintenance of location Effects 0.000 description 15
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 14
235000019439 ethyl acetate Nutrition 0.000 description 14
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
230000008878 coupling Effects 0.000 description 13
238000005859 coupling reaction Methods 0.000 description 13
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
239000003153 chemical reaction reagent Substances 0.000 description 12
239000012044 organic layer Substances 0.000 description 12
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
201000010099 disease Diseases 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
239000002253 acid Substances 0.000 description 9
229940125904 compound 1 Drugs 0.000 description 9
238000000113 differential scanning calorimetry Methods 0.000 description 9
239000003208 petroleum Substances 0.000 description 9
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
238000005481 NMR spectroscopy Methods 0.000 description 8
239000002585 base Substances 0.000 description 8
239000000460 chlorine Substances 0.000 description 7
239000007787 solid Substances 0.000 description 7
239000000725 suspension Substances 0.000 description 7
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
239000000651 prodrug Substances 0.000 description 6
229940002612 prodrug Drugs 0.000 description 6
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
150000001408 amides Chemical class 0.000 description 5
239000003480 eluent Substances 0.000 description 5
238000001914 filtration Methods 0.000 description 5
239000003446 ligand Substances 0.000 description 5
239000007788 liquid Substances 0.000 description 5
229910052943 magnesium sulfate Inorganic materials 0.000 description 5
235000019341 magnesium sulphate Nutrition 0.000 description 5
238000004519 manufacturing process Methods 0.000 description 5
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 5
229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
235000017557 sodium bicarbonate Nutrition 0.000 description 5
STBLNCCBQMHSRC-BATDWUPUSA-N (2s)-n-[(3s,4s)-5-acetyl-7-cyano-4-methyl-1-[(2-methylnaphthalen-1-yl)methyl]-2-oxo-3,4-dihydro-1,5-benzodiazepin-3-yl]-2-(methylamino)propanamide Chemical compound O=C1[C@@H](NC(=O)[C@H](C)NC)[C@H](C)N(C(C)=O)C2=CC(C#N)=CC=C2N1CC1=C(C)C=CC2=CC=CC=C12 STBLNCCBQMHSRC-BATDWUPUSA-N 0.000 description 4
KYWMCFOWDYFYLV-UHFFFAOYSA-N 1h-imidazole-2-carboxylic acid Chemical compound OC(=O)C1=NC=CN1 KYWMCFOWDYFYLV-UHFFFAOYSA-N 0.000 description 4
NMRZPULCVWCLQH-UHFFFAOYSA-N 2,5-dimethyl-1-phenylimidazole-4-carboxylic acid Chemical compound CC1=NC(C(O)=O)=C(C)N1C1=CC=CC=C1 NMRZPULCVWCLQH-UHFFFAOYSA-N 0.000 description 4
QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 description 4
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Chemical compound [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 4
210000000170 cell membrane Anatomy 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
229940125846 compound 25 Drugs 0.000 description 4
229940125878 compound 36 Drugs 0.000 description 4
WQOXQRCZOLPYPM-UHFFFAOYSA-N dimethyl disulfide Chemical compound CSSC WQOXQRCZOLPYPM-UHFFFAOYSA-N 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
VLDUBDZWWNLZCU-UHFFFAOYSA-N ethyl 5-methyl-1h-imidazole-4-carboxylate Chemical compound CCOC(=O)C=1NC=NC=1C VLDUBDZWWNLZCU-UHFFFAOYSA-N 0.000 description 4
239000011521 glass Substances 0.000 description 4
159000000011 group IA salts Chemical class 0.000 description 4
239000003921 oil Substances 0.000 description 4
235000019198 oils Nutrition 0.000 description 4
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
230000000144 pharmacologic effect Effects 0.000 description 4
238000000926 separation method Methods 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
239000002904 solvent Substances 0.000 description 4
150000003512 tertiary amines Chemical class 0.000 description 4
JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 4
WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 description 3
QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 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
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
230000004913 activation Effects 0.000 description 3
150000001602 bicycloalkyls Chemical group 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
229940126208 compound 22 Drugs 0.000 description 3
239000012043 crude product Substances 0.000 description 3
HJQQYURRTLCPPP-UHFFFAOYSA-N ethyl 1-benzyl-5-methylimidazole-4-carboxylate Chemical compound CC1=C(C(=O)OCC)N=CN1CC1=CC=CC=C1 HJQQYURRTLCPPP-UHFFFAOYSA-N 0.000 description 3
DZUREFWXAFXXCQ-UHFFFAOYSA-N ethyl 2-methyl-1-phenylimidazole-4-carboxylate Chemical compound CC1=NC(C(=O)OCC)=CN1C1=CC=CC=C1 DZUREFWXAFXXCQ-UHFFFAOYSA-N 0.000 description 3
235000019253 formic acid Nutrition 0.000 description 3
230000002140 halogenating effect Effects 0.000 description 3
238000000338 in vitro Methods 0.000 description 3
229910052740 iodine Inorganic materials 0.000 description 3
239000011630 iodine Substances 0.000 description 3
239000010410 layer Substances 0.000 description 3
OKXALXBKIMGQOO-UHFFFAOYSA-N methyl 2-acetamido-3-oxobutanoate Chemical compound COC(=O)C(C(C)=O)NC(C)=O OKXALXBKIMGQOO-UHFFFAOYSA-N 0.000 description 3
BORMPEPNKCKHJQ-UHFFFAOYSA-N n-(2,3-dichlorophenyl)-2,5-dimethyl-1-phenylimidazole-4-carboxamide Chemical compound CC=1N(C=2C=CC=CC=2)C(C)=NC=1C(=O)NC1=CC=CC(Cl)=C1Cl BORMPEPNKCKHJQ-UHFFFAOYSA-N 0.000 description 3
230000000269 nucleophilic effect Effects 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
125000006239 protecting group Chemical group 0.000 description 3
238000000746 purification Methods 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
229910000104 sodium hydride Inorganic materials 0.000 description 3
235000010288 sodium nitrite Nutrition 0.000 description 3
238000010561 standard procedure Methods 0.000 description 3
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238000002156 mixing Methods 0.000 description 1
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
RYTAVUUQISOHHK-UHFFFAOYSA-N n-(1-adamantyl)-2,5-dibromo-1-phenylimidazole-4-carboxamide Chemical compound BrC1=NC(C(=O)NC23CC4CC(CC(C4)C2)C3)=C(Br)N1C1=CC=CC=C1 RYTAVUUQISOHHK-UHFFFAOYSA-N 0.000 description 1
MDMQCHLOKAHLQV-UHFFFAOYSA-N n-(1-adamantyl)-2-methyl-1-phenylimidazole-4-carboxamide Chemical compound CC1=NC(C(=O)NC23CC4CC(CC(C4)C2)C3)=CN1C1=CC=CC=C1 MDMQCHLOKAHLQV-UHFFFAOYSA-N 0.000 description 1
HMGQFOSSMJOATQ-UHFFFAOYSA-N n-(1-adamantyl)-5-bromo-1-phenylimidazole-4-carboxamide Chemical compound BrC1=C(C(=O)NC23CC4CC(CC(C4)C2)C3)N=CN1C1=CC=CC=C1 HMGQFOSSMJOATQ-UHFFFAOYSA-N 0.000 description 1
YCJZWBZJSYLMPB-UHFFFAOYSA-N n-(2-chloropyrimidin-4-yl)-2,5-dimethyl-1-phenylimidazole-4-carboxamide Chemical compound CC=1N(C=2C=CC=CC=2)C(C)=NC=1C(=O)NC1=CC=NC(Cl)=N1 YCJZWBZJSYLMPB-UHFFFAOYSA-N 0.000 description 1
VGVVSDAEOBPQQA-UHFFFAOYSA-N n-(3-chloropropyl)methanesulfonamide Chemical compound CS(=O)(=O)NCCCCl VGVVSDAEOBPQQA-UHFFFAOYSA-N 0.000 description 1
SBBIJEPWFGSISW-UHFFFAOYSA-N n-methoxy-n,5-dimethyl-1-phenylimidazole-4-carboxamide Chemical compound CC1=C(C(=O)N(C)OC)N=CN1C1=CC=CC=C1 SBBIJEPWFGSISW-UHFFFAOYSA-N 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
208000004296 neuralgia Diseases 0.000 description 1
230000004770 neurodegeneration Effects 0.000 description 1
208000015122 neurodegenerative disease Diseases 0.000 description 1
208000021722 neuropathic pain Diseases 0.000 description 1
150000002826 nitrites Chemical class 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
125000005485 noradamantyl group Chemical group 0.000 description 1
239000012038 nucleophile Substances 0.000 description 1
239000002674 ointment Substances 0.000 description 1
PIDFDZJZLOTZTM-KHVQSSSXSA-N ombitasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)NC1=CC=C([C@H]2N([C@@H](CC2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)[C@@H](NC(=O)OC)C(C)C)=CC=2)C=2C=CC(=CC=2)C(C)(C)C)C=C1 PIDFDZJZLOTZTM-KHVQSSSXSA-N 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000002905 orthoesters Chemical class 0.000 description 1
125000002971 oxazolyl group Chemical group 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
239000003182 parenteral nutrition solution Substances 0.000 description 1
239000004031 partial agonist Substances 0.000 description 1
239000002245 particle Substances 0.000 description 1
235000020232 peanut Nutrition 0.000 description 1
238000010647 peptide synthesis reaction Methods 0.000 description 1
230000035699 permeability Effects 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
229940127557 pharmaceutical product Drugs 0.000 description 1
230000003285 pharmacodynamic effect Effects 0.000 description 1
125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
229920001983 poloxamer Polymers 0.000 description 1
229920001993 poloxamer 188 Polymers 0.000 description 1
229940044519 poloxamer 188 Drugs 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
125000002098 pyridazinyl group Chemical group 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical group C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
125000005493 quinolyl group Chemical group 0.000 description 1
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
239000002287 radioligand Substances 0.000 description 1
229940044601 receptor agonist Drugs 0.000 description 1
239000000018 receptor agonist Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000012552 review Methods 0.000 description 1
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
230000000391 smoking effect Effects 0.000 description 1
KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 description 1
208000020431 spinal cord injury Diseases 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
208000018556 stomach disease Diseases 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
239000002600 sunflower oil Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
230000005062 synaptic transmission Effects 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
230000008685 targeting Effects 0.000 description 1
238000012360 testing method Methods 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000004568 thiomorpholinyl group Chemical group 0.000 description 1
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
230000009529 traumatic brain injury Effects 0.000 description 1
VSRBKQFNFZQRBM-UHFFFAOYSA-N tuaminoheptane Chemical compound CCCCCC(C)N VSRBKQFNFZQRBM-UHFFFAOYSA-N 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
201000002498 viral encephalitis Diseases 0.000 description 1
238000003260 vortexing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
- 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
- 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
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Pain & Pain Management (AREA)
Immunology (AREA)
Rheumatology (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

BRPI0607439-1A 2005-02-16 2006-02-16 compostos, composição farmacêutica, método de preparação de composições farmacêuticas, e, uso de um composto BRPI0607439A2 (pt)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
US65309105P	2005-02-16	2005-02-16
EP05101171		2005-02-16
EP05101171.6		2005-02-16
US60/653,091		2005-02-16
PCT/EP2006/060009 WO2006087355A1 (en)	2005-02-16	2006-02-16	1h-imidiazole derivatives as cannabinoid cb2 receptor modulators

Publications (1)

Publication Number	Publication Date
BRPI0607439A2 true BRPI0607439A2 (pt)	2010-04-06

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BRPI0607439-1A BRPI0607439A2 (pt)	2005-02-16	2006-02-16	compostos, composição farmacêutica, método de preparação de composições farmacêuticas, e, uso de um composto

Country Status (9)

Country	Link
EP (1)	EP1874734A1 (no)
JP (1)	JP2008530179A (no)
AU (1)	AU2006215567B2 (no)
BR (1)	BRPI0607439A2 (no)
CA (1)	CA2597896A1 (no)
IL (1)	IL184006A0 (no)
NO (1)	NO20074710L (no)
RU (1)	RU2410377C2 (no)
WO (1)	WO2006087355A1 (no)

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TWI386405B (zh) *	2006-09-05	2013-02-21		咪唑衍生物
FR2908766B1 (fr) *	2006-11-20	2009-01-09	Sanofi Aventis Sa	Derives de pyrrole,leur preparation et leur utilisation en therapeutique.
EP2185506A1 (en) *	2007-08-22	2010-05-19	Allergan, Inc.	Pyrrole compounds having sphingosine-1-phosphate receptor agonist or antagonist biological activity
WO2009131957A2 (en)	2008-04-21	2009-10-29	Institute For Oneworld Health	Compounds, compositions and methods comprising oxadiazole derivatives
JP2012503005A (ja) *	2008-09-19	2012-02-02	インスティテュートフォアワンワールドヘルス	イミダゾール誘導体およびトリアゾール誘導体を含む、化合物、組成物ならびに方法。
KR20120117905A (ko)	2010-01-28	2012-10-24	프레지던트 앤드 펠로우즈 오브 하바드 칼리지	프로테아좀 활성을 향상시키는 조성물 및 방법
HUE044867T2 (hu)	2011-05-12	2019-11-28	Proteostasis Therapeutics Inc	Proteosztázis szabályzók
SG11201400974VA (en) *	2011-09-28	2014-09-26	Fujifilm Corp	Crystal of 5-hydroxy-1h-imidazole-4-carboxamideˑ3/4 hydrate, method for producing the same and crystal of 5-hydroxy-1h-imidazole-4-carboxamide hydrate
WO2013147160A1 (ja) *	2012-03-29	2013-10-03	東レ株式会社	環状アミン誘導体及びその医薬用途
US9849135B2 (en)	2013-01-25	2017-12-26	President And Fellows Of Harvard College	USP14 inhibitors for treating or preventing viral infections
CA2914997C (en) *	2013-06-12	2021-07-20	Kaken Pharmaceutical Co., Ltd.	4-alkynyl imidazole derivative and medicine comprising same as active ingredient
WO2015073528A1 (en)	2013-11-12	2015-05-21	Proteostasis Therapeutics, Inc.	Proteasome activity enhancing compounds
RU2018101897A (ru)	2015-06-22	2019-07-24	Сумитомо Дайниппон Фарма Ко., Лтд.	Бициклическое гетероциклическое амидное производное
CA2990583A1 (en) *	2015-06-22	2016-12-29	Sumitomo Dainippon Pharma Co., Ltd.	1,4-disubstituted imidazole derivative
JP6896701B2 (ja)	2016-02-26	2021-06-30	大日本住友製薬株式会社	イミダゾリルアミド誘導体
TW201803869A (zh)	2016-04-27	2018-02-01	健生藥品公司	作為ＲＯＲγＴ調節劑之６－胺基吡啶－３－基噻唑
ES2929140T3 (es) *	2018-06-18	2022-11-25	Janssen Pharmaceutica Nv	Imidazoles sustituidos con fenilo y piridinilo como moduladores de RORgammat
JP2021528398A (ja)	2018-06-18	2021-10-21	ヤンセンファーマシューティカエヌ．ベー．	ＲＯＲγＴのモジュレーターとしての６−アミノピリジン−３−イルピラゾール
JP2021528405A (ja)	2018-06-18	2021-10-21	ヤンセンファーマシューティカエヌ．ベー．	ＲＯＲγｔのモジュレータとしてのアミド置換チアゾール
EP3807261B1 (en)	2018-06-18	2022-07-13	Janssen Pharmaceutica NV	Pyridinyl pyrazoles as modulators of roryt
RU2725878C1 (ru) *	2019-12-30	2020-07-07	Федеральное государственное бюджетное учреждение науки Федеральный исследовательский центр "КОМИ научный центр Уральского отделения Российской академии наук"	Хиральные миртанилсульфонамиды

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RU2032671C1 (ru) *	1990-06-29	1995-04-10	Сумитомо Кемикал Компани Лимитед	Производные 1-фенилимидазола, проявляющие инсектицидные свойства, и инсектицидная композиция
EP1098885B9 (en) *	1998-07-23	2005-05-18	Fujisawa Pharmaceutical Co., Ltd.	Imidazole compounds and their use as adenosine deaminase inhibitors
WO2001058869A2 (en) *	2000-02-11	2001-08-16	Bristol-Myers Squibb Company	Cannabinoid receptor modulators, their processes of preparation, and use of cannabinoid receptor modulators in treating respiratory and non-respiratory diseases
JP5123668B2 (ja) *	2005-01-10	2013-01-23	エグゼリクシス，インコーポレイテッド	医薬品としての複素環カルボキサミド化合物

2006
- 2006-02-16 JP JP2007555612A patent/JP2008530179A/ja not_active Withdrawn
- 2006-02-16 EP EP06708303A patent/EP1874734A1/en not_active Withdrawn
- 2006-02-16 WO PCT/EP2006/060009 patent/WO2006087355A1/en not_active Ceased
- 2006-02-16 CA CA002597896A patent/CA2597896A1/en not_active Abandoned
- 2006-02-16 AU AU2006215567A patent/AU2006215567B2/en not_active Expired - Fee Related
- 2006-02-16 RU RU2007134428/04A patent/RU2410377C2/ru not_active IP Right Cessation
- 2006-02-16 BR BRPI0607439-1A patent/BRPI0607439A2/pt not_active IP Right Cessation
2007
- 2007-06-18 IL IL184006A patent/IL184006A0/en unknown
- 2007-09-14 NO NO20074710A patent/NO20074710L/no not_active Application Discontinuation

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EP1874734A1 (en)	2008-01-09
WO2006087355A1 (en)	2006-08-24
JP2008530179A (ja)	2008-08-07
IL184006A0 (en)	2007-10-31
NO20074710L (no)	2007-09-14
CA2597896A1 (en)	2006-08-24
RU2410377C2 (ru)	2011-01-27
AU2006215567A1 (en)	2006-08-24
RU2007134428A (ru)	2009-03-27
AU2006215567B2 (en)	2011-05-12

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Publication	Publication Date	Title
BRPI0607439A2 (pt)	2010-04-06	compostos, composição farmacêutica, método de preparação de composições farmacêuticas, e, uso de um composto
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