SK9222003A3 - Imidazolyl derivatives as corticotropin releasing factor inhibitors - Google Patents

Imidazolyl derivatives as corticotropin releasing factor inhibitors Download PDF

Info

Publication number: SK9222003A3
Authority: SK; Slovakia
Prior art keywords: alkyl; group; scheme; ylmethyl; trimethylphenyl
Prior art date: 2001-01-26

Application number

SK922-2003A

Other languages

English (en)

Slovak (sk)

Inventor

Gene M Dubowchik

Xiaojun Han

Vivekananda M Vrudhula

Dmitry Zuev

Bireshwar Dasgupta

Jodi A Michne

Original Assignee

Bristol Myers Squibb Co

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.)

2001-01-26

Filing date

2002-01-11

Publication date

2004-05-04

2002-01-11 Application filed by Bristol Myers Squibb Co filed Critical Bristol Myers Squibb Co

2004-05-04 Publication of SK9222003A3 publication Critical patent/SK9222003A3/sk

Links

108010022152 Corticotropin-Releasing Hormone Proteins 0.000 title description 25
239000000055 Corticotropin-Releasing Hormone Substances 0.000 title description 25
125000002883 imidazolyl group Chemical group 0.000 title description 3
239000003112 inhibitor Substances 0.000 title description 2
102000012289 Corticotropin-Releasing Hormone Human genes 0.000 title 1
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 17
229940079593 drug Drugs 0.000 claims abstract description 9
239000003814 drug Substances 0.000 claims abstract description 9
208000019901 Anxiety disease Diseases 0.000 claims abstract description 8
208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims abstract description 7
230000036506 anxiety Effects 0.000 claims abstract description 7
208000027866 inflammatory disease Diseases 0.000 claims abstract description 6
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
208000019454 Feeding and Eating disease Diseases 0.000 claims abstract description 5
206010019233 Headaches Diseases 0.000 claims abstract description 5
206010013663 drug dependence Diseases 0.000 claims abstract description 5
231100000869 headache Toxicity 0.000 claims abstract description 5
208000028173 post-traumatic stress disease Diseases 0.000 claims abstract description 5
208000019022 Mood disease Diseases 0.000 claims abstract description 4
208000011117 substance-related disease Diseases 0.000 claims abstract description 4
-1 m-alkoxy Chemical group 0.000 claims description 429
150000001875 compounds Chemical class 0.000 claims description 192
125000000217 alkyl group Chemical group 0.000 claims description 109
150000001412 amines Chemical class 0.000 claims description 73
125000004093 cyano group Chemical group *C#N 0.000 claims description 72
125000003545 alkoxy group Chemical group 0.000 claims description 58
239000002904 solvent Substances 0.000 claims description 47
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 46
229910052736 halogen Inorganic materials 0.000 claims description 44
150000002367 halogens Chemical class 0.000 claims description 41
125000004001 thioalkyl group Chemical group 0.000 claims description 40
229910052757 nitrogen Inorganic materials 0.000 claims description 37
125000005843 halogen group Chemical group 0.000 claims description 33
125000003118 aryl group Chemical group 0.000 claims description 30
125000000753 cycloalkyl group Chemical group 0.000 claims description 30
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
125000002947 alkylene group Chemical group 0.000 claims description 28
SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 27
125000000304 alkynyl group Chemical group 0.000 claims description 26
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 25
125000001424 substituent group Chemical group 0.000 claims description 23
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
238000000034 method Methods 0.000 claims description 21
125000003342 alkenyl group Chemical group 0.000 claims description 20
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 19
229910052739 hydrogen Inorganic materials 0.000 claims description 19
125000001188 haloalkyl group Chemical group 0.000 claims description 18
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
239000001257 hydrogen Substances 0.000 claims description 17
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 15
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 15
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 15
239000000460 chlorine Substances 0.000 claims description 14
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 14
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 13
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 12
125000001309 chloro group Chemical group Cl* 0.000 claims description 11
125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 10
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
125000001769 aryl amino 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
208000035475 disorder Diseases 0.000 claims description 10
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 9
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 9
229910052801 chlorine Inorganic materials 0.000 claims description 9
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 9
150000003839 salts Chemical class 0.000 claims description 9
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
229910052794 bromium Inorganic materials 0.000 claims description 8
239000003880 polar aprotic solvent Substances 0.000 claims description 8
229910052717 sulfur Inorganic materials 0.000 claims description 8
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
125000004076 pyridyl group Chemical group 0.000 claims description 7
125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 6
125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 6
229910014033 C-OH Inorganic materials 0.000 claims description 6
229910014570 C—OH Inorganic materials 0.000 claims description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
229910052760 oxygen Inorganic materials 0.000 claims description 6
230000007958 sleep Effects 0.000 claims description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
206010020772 Hypertension Diseases 0.000 claims description 5
229910052731 fluorine Inorganic materials 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
239000012453 solvate Substances 0.000 claims description 5
125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 5
KPPVNWGJXFMGAM-UUILKARUSA-N (e)-2-methyl-1-(6-methyl-3,4-dihydro-2h-quinolin-1-yl)but-2-en-1-one Chemical compound CC1=CC=C2N(C(=O)C(/C)=C/C)CCCC2=C1 KPPVNWGJXFMGAM-UUILKARUSA-N 0.000 claims description 4
KIPSRYDSZQRPEA-UHFFFAOYSA-N 2,2,2-trifluoroethanamine Chemical compound NCC(F)(F)F KIPSRYDSZQRPEA-UHFFFAOYSA-N 0.000 claims description 4
201000006474 Brain Ischemia Diseases 0.000 claims description 4
206010008120 Cerebral ischaemia Diseases 0.000 claims description 4
208000030814 Eating disease Diseases 0.000 claims description 4
208000006011 Stroke Diseases 0.000 claims description 4
206010042434 Sudden death Diseases 0.000 claims description 4
208000025865 Ulcer Diseases 0.000 claims description 4
125000001118 alkylidene group Chemical group 0.000 claims description 4
238000009835 boiling Methods 0.000 claims description 4
206010008118 cerebral infarction Diseases 0.000 claims description 4
235000014632 disordered eating Nutrition 0.000 claims description 4
125000001153 fluoro group Chemical group F* 0.000 claims description 4
125000005842 heteroatom Chemical group 0.000 claims description 4
230000004112 neuroprotection Effects 0.000 claims description 4
125000002560 nitrile group Chemical group 0.000 claims description 4
GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 claims description 4
208000011580 syndromic disease Diseases 0.000 claims description 4
231100000397 ulcer Toxicity 0.000 claims description 4
DVZTWZCNZAQYBD-UHFFFAOYSA-N 2-chloro-1-(2,4-dichlorophenyl)-6-ethylimidazo[1,2-a]imidazole-5-carboxylic acid Chemical compound ClC1=CN2C(C(O)=O)=C(CC)N=C2N1C1=CC=C(Cl)C=C1Cl DVZTWZCNZAQYBD-UHFFFAOYSA-N 0.000 claims description 3
206010010904 Convulsion Diseases 0.000 claims description 3
206010012735 Diarrhoea Diseases 0.000 claims description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
208000008589 Obesity Diseases 0.000 claims description 3
206010054048 Postoperative ileus Diseases 0.000 claims description 3
208000006399 Premature Obstetric Labor Diseases 0.000 claims description 3
206010036600 Premature labour Diseases 0.000 claims description 3
208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 claims description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
125000005275 alkylenearyl group Chemical group 0.000 claims description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
229910052799 carbon Inorganic materials 0.000 claims description 3
206010015037 epilepsy Diseases 0.000 claims description 3
239000011737 fluorine Substances 0.000 claims description 3
208000037824 growth disorder Diseases 0.000 claims description 3
208000019622 heart disease Diseases 0.000 claims description 3
208000000509 infertility Diseases 0.000 claims description 3
230000036512 infertility Effects 0.000 claims description 3
231100000535 infertility Toxicity 0.000 claims description 3
206010022437 insomnia Diseases 0.000 claims description 3
JHBCBRNXFUKWPZ-UHFFFAOYSA-N n-[[2-chloro-6-ethyl-1-(2,4,6-trimethylphenyl)imidazo[1,2-a]imidazol-5-yl]methyl]-n-(cyclopropylmethyl)ethanamine Chemical compound CCC=1N=C2N(C=3C(=CC(C)=CC=3C)C)C(Cl)=CN2C=1CN(CC)CC1CC1 JHBCBRNXFUKWPZ-UHFFFAOYSA-N 0.000 claims description 3
235000020824 obesity Nutrition 0.000 claims description 3
239000001301 oxygen Chemical group 0.000 claims description 3
230000002980 postoperative effect Effects 0.000 claims description 3
208000026440 premature labor Diseases 0.000 claims description 3
239000011593 sulfur Chemical group 0.000 claims description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 2
125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 2
208000001871 Tachycardia Diseases 0.000 claims description 2
125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 2
208000002551 irritable bowel syndrome Diseases 0.000 claims description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 claims description 2
VXPLXMJHHKHSOA-UHFFFAOYSA-N propham Chemical compound CC(C)OC(=O)NC1=CC=CC=C1 VXPLXMJHHKHSOA-UHFFFAOYSA-N 0.000 claims description 2
230000006794 tachycardia Effects 0.000 claims description 2
208000014644 Brain disease Diseases 0.000 claims 1
125000006383 alkylpyridyl group Chemical group 0.000 claims 1
125000004430 oxygen atom Chemical group O* 0.000 claims 1
230000000472 traumatic effect Effects 0.000 claims 1
108010056643 Corticotropin-Releasing Hormone Receptors Proteins 0.000 abstract description 12
239000005557 antagonist Substances 0.000 abstract description 12
108091005471 CRHR1 Proteins 0.000 abstract description 7
208000020401 Depressive disease Diseases 0.000 abstract description 4
108020003175 receptors Proteins 0.000 abstract description 3
208000029650 alcohol withdrawal Diseases 0.000 abstract description 2
230000008485 antagonism Effects 0.000 abstract description 2
239000003488 releasing hormone Substances 0.000 abstract description 2
208000024891 symptom Diseases 0.000 abstract 1
238000005481 NMR spectroscopy Methods 0.000 description 187
239000000543 intermediate Substances 0.000 description 185
238000004949 mass spectrometry Methods 0.000 description 159
239000000243 solution Substances 0.000 description 143
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 132
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 129
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 114
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 70
239000000203 mixture Substances 0.000 description 69
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 59
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WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 37
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CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 30
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 28
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 27
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 26
102100021752 Corticoliberin Human genes 0.000 description 25
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 25
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 23
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 22
238000001816 cooling Methods 0.000 description 22
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 21
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 19
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
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238000013421 nuclear magnetic resonance imaging Methods 0.000 description 16
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235000019341 magnesium sulphate Nutrition 0.000 description 15
239000012044 organic layer Substances 0.000 description 14
238000003756 stirring Methods 0.000 description 14
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
238000004811 liquid chromatography Methods 0.000 description 13
239000000284 extract Substances 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 11
238000004587 chromatography analysis Methods 0.000 description 11
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
241000700159 Rattus Species 0.000 description 10
210000004556 brain Anatomy 0.000 description 10
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 10
238000000746 purification Methods 0.000 description 10
150000001408 amides Chemical class 0.000 description 9
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WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 9
238000004007 reversed phase HPLC Methods 0.000 description 9
235000017557 sodium bicarbonate Nutrition 0.000 description 9
229910000030 sodium bicarbonate Inorganic materials 0.000 description 9
229910052938 sodium sulfate Inorganic materials 0.000 description 9
235000011152 sodium sulphate Nutrition 0.000 description 9
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 9
125000004494 ethyl ester group Chemical group 0.000 description 8
238000001914 filtration Methods 0.000 description 8
239000003921 oil Substances 0.000 description 8
238000010992 reflux Methods 0.000 description 8
229920006395 saturated elastomer Polymers 0.000 description 8
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 7
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KLVRDXBAMSPYKH-RKYZNNDCSA-N corticotropin-releasing hormone (human) Chemical compound C([C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@H](C(=O)N[C@@H]([C@@H](C)CC)C(N)=O)[C@@H](C)CC)NC(=O)[C@H](C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](C)NC(=O)[C@H](CCSC)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H]1N(CCC1)C(=O)[C@H]1N(CCC1)C(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@@H](N)CO)[C@@H](C)CC)C(C)C)C(C)C)C1=CNC=N1 KLVRDXBAMSPYKH-RKYZNNDCSA-N 0.000 description 7
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ADOYIMJMJBWVRW-UHFFFAOYSA-N ethyl 1-(2-bromo-4-propan-2-ylphenyl)-6-ethyl-2,3-dihydroimidazo[1,2-a]imidazole-5-carboxylate Chemical compound C1CN2C(C(=O)OCC)=C(CC)N=C2N1C1=CC=C(C(C)C)C=C1Br ADOYIMJMJBWVRW-UHFFFAOYSA-N 0.000 description 1
UPOXRKXHTQVXJU-UHFFFAOYSA-N ethyl 1-(2-bromo-4-propan-2-ylphenyl)-6-ethyl-2-oxo-3h-imidazo[1,2-a]imidazole-5-carboxylate Chemical compound O=C1CN2C(C(=O)OCC)=C(CC)N=C2N1C1=CC=C(C(C)C)C=C1Br UPOXRKXHTQVXJU-UHFFFAOYSA-N 0.000 description 1
QWJSQTABTVAGBF-UHFFFAOYSA-N ethyl 1-(2-chloro-4,6-dimethylphenyl)-6-ethyl-2-oxo-3h-imidazo[1,2-a]imidazole-5-carboxylate Chemical compound O=C1CN2C(C(=O)OCC)=C(CC)N=C2N1C1=C(C)C=C(C)C=C1Cl QWJSQTABTVAGBF-UHFFFAOYSA-N 0.000 description 1
DZIJEAXVLBWTFB-UHFFFAOYSA-N ethyl 2-(trifluoromethyl)-4-(2,4,6-trimethylphenyl)imidazo[1,2-a]benzimidazole-1-carboxylate Chemical compound C12=CC=CC=C2N2C(C(=O)OCC)=C(C(F)(F)F)N=C2N1C1=C(C)C=C(C)C=C1C DZIJEAXVLBWTFB-UHFFFAOYSA-N 0.000 description 1
AHKJRMXWDUPQPV-UHFFFAOYSA-N ethyl 2-(trifluoromethyl)-8-(2,4,6-trimethylphenyl)-6,7-dihydro-5h-imidazo[1,2-a]pyrimidine-3-carboxylate Chemical compound C1CCN2C(C(=O)OCC)=C(C(F)(F)F)N=C2N1C1=C(C)C=C(C)C=C1C AHKJRMXWDUPQPV-UHFFFAOYSA-N 0.000 description 1
ZXUCZZRLAQYGPU-UHFFFAOYSA-N ethyl 2-[2-amino-3-(2,4,6-trimethylphenyl)benzimidazol-1-ium-1-yl]acetate bromide Chemical compound [Br-].CCOC(=O)C[N+]1=C(N)N(C2=CC=CC=C12)C1=C(C)C=C(C)C=C1C ZXUCZZRLAQYGPU-UHFFFAOYSA-N 0.000 description 1
WOIDEONWPRUYOR-UHFFFAOYSA-N ethyl 2-[2-amino-3-(2,4-dichlorophenyl)benzimidazol-1-ium-1-yl]acetate bromide Chemical compound [Br-].CCOC(=O)C[N+]1=C(N)N(C2=CC=CC=C12)C1=CC=C(Cl)C=C1Cl WOIDEONWPRUYOR-UHFFFAOYSA-N 0.000 description 1
SXTKJJRCOVWYGH-UHFFFAOYSA-N ethyl 2-[2-amino-3-(2-bromo-4-propan-2-ylphenyl)benzimidazol-1-ium-1-yl]acetate;bromide Chemical compound [Br-].C12=CC=CC=C2[N+](CC(=O)OCC)=C(N)N1C1=CC=C(C(C)C)C=C1Br SXTKJJRCOVWYGH-UHFFFAOYSA-N 0.000 description 1
SXAASATYTNZMKN-UHFFFAOYSA-N ethyl 2-bromo-3-[2-(2,4-dichloroanilino)-2-oxoethyl]-5-ethylimidazole-4-carboxylate Chemical compound CCOC(=O)C1=C(CC)N=C(Br)N1CC(=O)NC1=CC=C(Cl)C=C1Cl SXAASATYTNZMKN-UHFFFAOYSA-N 0.000 description 1
YENZQADGYCJMBO-UHFFFAOYSA-N ethyl 2-bromo-3-[2-(2-bromo-4-propan-2-ylanilino)-2-oxoethyl]-5-ethylimidazole-4-carboxylate Chemical compound CCOC(=O)C1=C(CC)N=C(Br)N1CC(=O)NC1=CC=C(C(C)C)C=C1Br YENZQADGYCJMBO-UHFFFAOYSA-N 0.000 description 1
SOHFKURBPSLQOD-UHFFFAOYSA-N ethyl 2-bromo-3-[2-(2-chloro-4,6-dimethylanilino)-2-oxoethyl]-5-ethylimidazole-4-carboxylate Chemical compound CCOC(=O)C1=C(CC)N=C(Br)N1CC(=O)NC1=C(C)C=C(C)C=C1Cl SOHFKURBPSLQOD-UHFFFAOYSA-N 0.000 description 1
NCXBBHOYTUTPDX-UHFFFAOYSA-N ethyl 2-bromo-3-[3-(2-chloro-4,6-dimethylanilino)propyl]-5-(trifluoromethyl)imidazole-4-carboxylate Chemical compound CCOC(=O)C1=C(C(F)(F)F)N=C(Br)N1CCCNC1=C(C)C=C(C)C=C1Cl NCXBBHOYTUTPDX-UHFFFAOYSA-N 0.000 description 1
VHSMVVWMAHWZER-UHFFFAOYSA-N ethyl 2-bromo-5-(trifluoromethyl)-1h-imidazole-4-carboxylate Chemical compound CCOC(=O)C=1NC(Br)=NC=1C(F)(F)F VHSMVVWMAHWZER-UHFFFAOYSA-N 0.000 description 1
HTCCQEPSMDWSAQ-UHFFFAOYSA-N ethyl 2-bromo-5-(trifluoromethyl)-3-[3-(2,4,6-trimethylanilino)propyl]imidazole-4-carboxylate Chemical compound CCOC(=O)C1=C(C(F)(F)F)N=C(Br)N1CCCNC1=C(C)C=C(C)C=C1C HTCCQEPSMDWSAQ-UHFFFAOYSA-N 0.000 description 1
WPGMVLCBAXSBLG-UHFFFAOYSA-N ethyl 2-bromo-5-ethyl-3-[2-oxo-2-(2,4,6-trichloroanilino)ethyl]imidazole-4-carboxylate Chemical compound CCOC(=O)C1=C(CC)N=C(Br)N1CC(=O)NC1=C(Cl)C=C(Cl)C=C1Cl WPGMVLCBAXSBLG-UHFFFAOYSA-N 0.000 description 1
ZLFMVIUJONBKIY-UHFFFAOYSA-N ethyl 2-bromo-5-ethyl-3-[2-oxo-2-(2,4,6-trimethylanilino)ethyl]imidazole-4-carboxylate Chemical compound CCOC(=O)C1=C(CC)N=C(Br)N1CC(=O)NC1=C(C)C=C(C)C=C1C ZLFMVIUJONBKIY-UHFFFAOYSA-N 0.000 description 1
IMURCVXTXPJISF-UHFFFAOYSA-N ethyl 2-bromo-5-ethyl-3-[3-(2,4,6-trimethylanilino)propyl]imidazole-4-carboxylate Chemical compound CCOC(=O)C1=C(CC)N=C(Br)N1CCCNC1=C(C)C=C(C)C=C1C IMURCVXTXPJISF-UHFFFAOYSA-N 0.000 description 1
LYNIJZZYBZLQCU-UHFFFAOYSA-N ethyl 2-bromo-5-methyl-1h-imidazole-4-carboxylate Chemical compound CCOC(=O)C=1NC(Br)=NC=1C LYNIJZZYBZLQCU-UHFFFAOYSA-N 0.000 description 1
ZLMQKCQUIGPRHE-UHFFFAOYSA-N ethyl 2-bromo-5-methyl-3-[3-(2,4,6-trimethylanilino)propyl]imidazole-4-carboxylate Chemical compound CCOC(=O)C1=C(C)N=C(Br)N1CCCNC1=C(C)C=C(C)C=C1C ZLMQKCQUIGPRHE-UHFFFAOYSA-N 0.000 description 1
IJKXXJIUCLSQGQ-UHFFFAOYSA-N ethyl 2-chloro-1-(2,4-dichlorophenyl)-6-ethylimidazo[1,2-a]imidazole-5-carboxylate Chemical compound ClC1=CN2C(C(=O)OCC)=C(CC)N=C2N1C1=CC=C(Cl)C=C1Cl IJKXXJIUCLSQGQ-UHFFFAOYSA-N 0.000 description 1
ZZXRFDRKCWTRGV-UHFFFAOYSA-N ethyl 2-chloro-1-(2-chloro-4,6-dimethylphenyl)-6-ethylimidazo[1,2-a]imidazole-5-carboxylate Chemical compound ClC1=CN2C(C(=O)OCC)=C(CC)N=C2N1C1=C(C)C=C(C)C=C1Cl ZZXRFDRKCWTRGV-UHFFFAOYSA-N 0.000 description 1
QWWAOWHSFLLVMB-UHFFFAOYSA-N ethyl 2-chloro-6-ethyl-1-(2,4,6-trichlorophenyl)imidazo[1,2-a]imidazole-5-carboxylate Chemical compound ClC1=CN2C(C(=O)OCC)=C(CC)N=C2N1C1=C(Cl)C=C(Cl)C=C1Cl QWWAOWHSFLLVMB-UHFFFAOYSA-N 0.000 description 1
XBXPQZNIEBSIAJ-UHFFFAOYSA-N ethyl 2-chloro-6-ethyl-1-(2,4,6-trimethylphenyl)imidazo[1,2-a]imidazole-5-carboxylate Chemical compound ClC1=CN2C(C(=O)OCC)=C(CC)N=C2N1C1=C(C)C=C(C)C=C1C XBXPQZNIEBSIAJ-UHFFFAOYSA-N 0.000 description 1
UPFRPOBRHLVGJZ-UHFFFAOYSA-N ethyl 2-ethyl-4-(2,4,6-trimethylphenyl)imidazo[1,2-a]benzimidazole-1-carboxylate Chemical compound C12=CC=CC=C2N2C(C(=O)OCC)=C(CC)N=C2N1C1=C(C)C=C(C)C=C1C UPFRPOBRHLVGJZ-UHFFFAOYSA-N 0.000 description 1
UQLREXKPBAOKLX-UHFFFAOYSA-N ethyl 2-ethyl-4-(2,4,6-trimethylphenyl)imidazo[1,2]imidazo[2,3-b]pyridine-1-carboxylate Chemical compound C12=NC=CC=C2N2C(C(=O)OCC)=C(CC)N=C2N1C1=C(C)C=C(C)C=C1C UQLREXKPBAOKLX-UHFFFAOYSA-N 0.000 description 1
XGJSNFRPRVDWBJ-UHFFFAOYSA-N ethyl 2-ethyl-7-fluoro-4-(2,4,6-trimethylphenyl)imidazo[1,2-a]benzimidazole-1-carboxylate Chemical compound C12=CC=C(F)C=C2N2C(C(=O)OCC)=C(CC)N=C2N1C1=C(C)C=C(C)C=C1C XGJSNFRPRVDWBJ-UHFFFAOYSA-N 0.000 description 1
IBXGKYYISXQNNE-UHFFFAOYSA-N ethyl 2-ethyl-8-(2,4,6-trimethylphenyl)-6,7-dihydro-5h-imidazo[1,2-a]pyrimidine-3-carboxylate Chemical compound C1CCN2C(C(=O)OCC)=C(CC)N=C2N1C1=C(C)C=C(C)C=C1C IBXGKYYISXQNNE-UHFFFAOYSA-N 0.000 description 1
ZFEOWGLVGDEFQZ-UHFFFAOYSA-N ethyl 2-methyl-4-(2,4,6-trimethylphenyl)imidazo[1,2-a]benzimidazole-1-carboxylate Chemical compound C12=CC=CC=C2N2C(C(=O)OCC)=C(C)N=C2N1C1=C(C)C=C(C)C=C1C ZFEOWGLVGDEFQZ-UHFFFAOYSA-N 0.000 description 1
RGQGAQMUJCXFHR-UHFFFAOYSA-N ethyl 2-methyl-4-(2,4,6-trimethylphenyl)imidazo[1,2]imidazo[2,3-b]pyridine-1-carboxylate Chemical compound C12=NC=CC=C2N2C(C(=O)OCC)=C(C)N=C2N1C1=C(C)C=C(C)C=C1C RGQGAQMUJCXFHR-UHFFFAOYSA-N 0.000 description 1
PJMUYYGDXCPMME-UHFFFAOYSA-N ethyl 2-methyl-6-oxo-7-(2,4,6-trimethylphenyl)-1,5-dihydroimidazo[1,2-a]imidazol-4-ium-3-carboxylate;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.O=C1CN2C(C(=O)OCC)=C(C)[NH+]=C2N1C1=C(C)C=C(C)C=C1C PJMUYYGDXCPMME-UHFFFAOYSA-N 0.000 description 1
BSSJJYLMFIIGMQ-UHFFFAOYSA-N ethyl 2-methyl-6-oxo-7-(2,4,6-trimethylphenyl)-5h-imidazo[1,2-a]imidazole-3-carboxylate Chemical compound O=C1CN2C(C(=O)OCC)=C(C)N=C2N1C1=C(C)C=C(C)C=C1C BSSJJYLMFIIGMQ-UHFFFAOYSA-N 0.000 description 1
HRBKVPQNYMTKML-UHFFFAOYSA-N ethyl 2-methyl-8-(2,4,6-trimethylphenyl)-6,7-dihydro-5h-imidazo[1,2-a]pyrimidine-3-carboxylate Chemical compound C1CCN2C(C(=O)OCC)=C(C)N=C2N1C1=C(C)C=C(C)C=C1C HRBKVPQNYMTKML-UHFFFAOYSA-N 0.000 description 1
NHVMRZIKJFZGFC-UHFFFAOYSA-N ethyl 4-(2,4-dichlorophenyl)-2-methylimidazo[1,2-a]benzimidazole-1-carboxylate Chemical compound C12=CC=CC=C2N2C(C(=O)OCC)=C(C)N=C2N1C1=CC=C(Cl)C=C1Cl NHVMRZIKJFZGFC-UHFFFAOYSA-N 0.000 description 1
ZPZGKSMCMWCGEL-UHFFFAOYSA-N ethyl 4-(2-bromo-4-propan-2-ylphenyl)-2-(trifluoromethyl)imidazo[1,2-a]benzimidazole-1-carboxylate Chemical compound C12=CC=CC=C2N2C(C(=O)OCC)=C(C(F)(F)F)N=C2N1C1=CC=C(C(C)C)C=C1Br ZPZGKSMCMWCGEL-UHFFFAOYSA-N 0.000 description 1
GJTOPYNDCQPWKE-UHFFFAOYSA-N ethyl 4-(2-chloro-4,6-dimethylphenyl)-2-methylimidazo[1,2]imidazo[2,3-b]pyridine-1-carboxylate Chemical compound C12=NC=CC=C2N2C(C(=O)OCC)=C(C)N=C2N1C1=C(C)C=C(C)C=C1Cl GJTOPYNDCQPWKE-UHFFFAOYSA-N 0.000 description 1
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SK922-2003A 2001-01-26 2002-01-11 Imidazolyl derivatives as corticotropin releasing factor inhibitors SK9222003A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US26457001P	2001-01-26	2001-01-26
PCT/US2002/000841 WO2002058704A1 (en)	2001-01-26	2002-01-11	Imidazolyl derivatives as corticotropin releasing factor inhibitors

Publications (1)

Publication Number	Publication Date
SK9222003A3 true SK9222003A3 (en)	2004-05-04

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SK922-2003A SK9222003A3 (en)	2001-01-26	2002-01-11	Imidazolyl derivatives as corticotropin releasing factor inhibitors

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US (5)	US6888004B2 (cs)
EP (1)	EP1359916A4 (cs)
JP (1)	JP2004531475A (cs)
KR (1)	KR20040034594A (cs)
CN (1)	CN1499972A (cs)
BG (1)	BG107999A (cs)
BR (1)	BR0206698A (cs)
CA (1)	CA2434558A1 (cs)
CZ (1)	CZ20032044A3 (cs)
EE (1)	EE200300342A (cs)
HR (1)	HRP20030675A2 (cs)
HU (1)	HUP0303721A2 (cs)
IL (1)	IL156813A0 (cs)
IS (1)	IS6889A (cs)
MX (1)	MXPA03006484A (cs)
NO (1)	NO20033350L (cs)
PE (1)	PE20020844A1 (cs)
PL (1)	PL368555A1 (cs)
RU (1)	RU2003126188A (cs)
SK (1)	SK9222003A3 (cs)
WO (1)	WO2002058704A1 (cs)
ZA (1)	ZA200305531B (cs)

Families Citing this family (24)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
KR20040034594A (ko) *	2001-01-26	2004-04-28	브리스톨-마이어스스퀴브컴파니	코르티코트로핀 방출 인자 억제제로서의 이미다졸릴 유도체
TWI312347B (en)	2001-02-08	2009-07-21	Eisai R&D Man Co Ltd	Bicyclic nitrogen-containing condensed ring compounds
HUP0401292A3 (en)	2001-04-27	2011-01-28	Eisai R & D Man Co	Pyrazolo[1,5-a]pyridines, pharmaceutical compositions containing the same and process for preparation thereof
TWI283679B (en)	2002-10-22	2007-07-11	Eisai Co Ltd	7-phenylpyrazolopyridine compounds
US7176216B2 (en)	2002-10-22	2007-02-13	Eisai Co., Ltd.	7-phenylpyrazolopyridine compounds
WO2006065793A2 (en) *	2004-12-13	2006-06-22	Indevus Pharmaceuticals, Inc.	TREATMENT OF INTERSTITIAL CYSTITIS USING (6aR,10aR)-Δ8-TETRAHYDROCANNABINOL-11-OIC ACIDS
WO2007090087A2 (en) *	2006-01-27	2007-08-09	Research Development Foundation	Use of corticotropin releasing factor receptor-2 inhibitors for treating insulin-related diseases
EP2167094A2 (en)	2007-06-13	2010-03-31	Research Development Foundation	Methods for treatment and prevention of tauopathies and amyloid beta amyloidosis by modulating crf receptor signaling
MX2010004995A (es) *	2007-11-29	2010-05-20	Boehringer Ingelheim Int	Derivados de amidas del acido 6,7-dihidro-5h-imidazo[1,2-a]imidazo l-3-carboxilico.
EP2266990B1 (en)	2008-04-15	2012-09-26	Eisai R&D Management Co., Ltd.	3-PHENYLPYRAZOLO[5,1-b]THIAZOLE COMPOUND
US7994203B2 (en) *	2008-08-06	2011-08-09	Novartis Ag	Organic compounds
AR078521A1 (es)	2009-10-08	2011-11-16	Eisai R&D Man Co Ltd	Compuesto pirazolotiazol
JP2013518085A (ja) *	2010-02-01	2013-05-20	ノバルティスアーゲー	ＣＲＦ−１受容体アンタゴニストとしてのピラゾロ［５，１ｂ］オキサゾール誘導体
US9806270B2 (en) *	2011-03-25	2017-10-31	Udc Ireland Limited	4H-imidazo[1,2-a]imidazoles for electronic applications
KR102266455B1 (ko) *	2011-03-25	2021-06-21	유디씨 아일랜드 리미티드	전자장치 응용을 위한 4h-이미다조[1,2-a]이미다졸
US9502664B2 (en)	2011-11-10	2016-11-22	Udc Ireland Limited	4H-imidazo[1,2-a]imidazoles for electronic applications
CN109970707A (zh) *	2012-02-07	2019-07-05	拜耳知识产权有限责任公司	取代的邻氨基苯甲酸衍生物的制备方法
IN2014DN10229A (cs)	2012-05-25	2015-08-07	Nutech Ventures
EP3232485A1 (en)	2012-07-10	2017-10-18	UDC Ireland Limited	Benzimidazo[1,2-a]benzimidazole derivatives for electronic applications
US9605002B2 (en) *	2012-07-18	2017-03-28	University Of Notre Dame Du Lac	5,5-heteroaromatic anti-infective compounds
US20140206667A1 (en)	2012-11-14	2014-07-24	Michela Gallagher	Methods and compositions for treating schizophrenia
CN105384691B (zh) *	2015-10-26	2018-06-29	深圳大学	一种谷氨酰胺酰基环化酶抑制剂的制备方法及应用
WO2019022873A1 (en) *	2017-07-24	2019-01-31	University Of South Florida	NEW BIS-CYCLIC GUANIDINES USEFUL AS ANTIBACTERIAL AGENTS
US10729693B2 (en) *	2018-03-02	2020-08-04	Ponce Medical School Foundation, Inc.	Compositions and methods for the treatment of endometriosis

Family Cites Families (30)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3865836A (en) *	1972-12-08	1975-02-11	Janssen Pharmaceutica Nv	Bicyclic imidazoles
DE2827617A1 (de) *	1978-06-23	1980-01-10	Boehringer Sohn Ingelheim	Neue imidazo eckige klammer auf 1,2- alpha eckige klammer zu imidazole, deren saeureadditionssalze, diese enthaltende arzneimittel und verfahren zu deren herstellung
IL69417A (en) *	1982-08-27	1987-12-20	Roussel Uclaf	2-acyl imidazo(1,2-a)pyrimidines,their preparation and pharmaceutical compositions containing them
US4551530A (en) *	1984-11-19	1985-11-05	American Cyanamid Company	Pyridyl imidazo[1,2-a]pyrimidines
DK155524C (da) *	1987-03-18	1989-09-11	Ferrosan As	Kondenserede imidazolderivater og farmaceutiske praeparater indeholdende disse
JPH05107705A (ja) *	1991-10-17	1993-04-30	Konica Corp	新規な写真用カプラー
DK0571253T3 (da) *	1992-05-19	1999-07-19	Adir	Benzimidazolderivater med antidiabetisk og antiblodpladekoagulerende virkning
EP0607076A1 (fr) *	1993-01-15	1994-07-20	Synthelabo	Dérivés de 9h-imidazo 1,2-a benzimidazole-3-acétamide à activité GABA
FR2722501B1 (fr) *	1994-07-13	1996-08-09	Synthelabo	Derives de 9h-imidazo(1,2-a)benzimidazole-3-acetamide, leur preparation et leur application en therapeutique
PT778277E (pt)	1995-12-08	2003-11-28	Pfizer	Derivados heterociclicos substituidos como antagonistas do crf
AU713673B2 (en) *	1996-02-07	1999-12-09	Neurocrine Biosciences Inc.	Pyrazolopyrimidines as crf receptor antagonists
US6022978A (en)	1996-06-11	2000-02-08	Pfizer Inc.	Benzimidazole derivatives
WO1998014452A1 (en) *	1996-10-03	1998-04-09	Nissan Chemical Industries, Ltd.	Heterocycle-fused pyrimidinone derivatives and herbicides
AU6279598A (en)	1997-02-18	1998-09-08	Neurocrine Biosciences, Inc.	Biazacyclic CRF antagonists
PL337888A1 (en)	1997-07-03	2000-09-11	Du Pont Pharm Co	Imidazoprimidines and imidazopyridines for use in treating neurological disorders
WO1999010350A1 (en)	1997-08-22	1999-03-04	Du Pont Pharmaceuticals Company	NITROGEN SUBSTITUTED IMIDAZO[4,5-c]PYRAZOLES AS CORTICOTROPIN RELEASING HORMONE ANTAGONISTS
BR9803368A (pt) *	1997-09-05	2001-04-24	Sumitomo Chemical Co	Derivados de perimidona e herbecidas contendo os mesmos
AU1520699A (en) *	1997-11-07	1999-05-31	Johns Hopkins University, The	Methods for treatment of disorders of cardiac contractility
US6194419B1 (en) *	1997-12-26	2001-02-27	Takeda Chemical Industries, Ltd.	Nitrogen-containing heterocyclic compounds, their production and use
US6509338B1 (en)	1998-06-22	2003-01-21	Bristol-Myers Squibb Company	Pyrazolo[1,5-A]triazine corticotropin releasing factor antagonists
US6365589B1 (en)	1998-07-02	2002-04-02	Bristol-Myers Squibb Pharma Company	Imidazo-pyridines, -pyridazines, and -triazines as corticotropin releasing factor antagonists
US6124463A (en)	1998-07-02	2000-09-26	Dupont Pharmaceuticals	Benzimidazoles as corticotropin release factor antagonists
US6271380B1 (en)	1998-12-30	2001-08-07	Dupont Pharmaceuticals Company	1H-imidazo[4,5-d]pyridazin-7-ones, 3H-imidazo-[4,5-c]pyridin-4-ones and corresponding thiones as corticotropin releasing factor (CRF) receptor ligands
AU4203500A (en)	1999-04-06	2000-10-23	Du Pont Pharmaceuticals Company	Pyrazolopyrimidines as crf antagonists
AU4331500A (en)	1999-04-06	2000-10-23	Du Pont Pharmaceuticals Company	Pyrazolotriazines as crf antagonists
US6492408B1 (en) *	1999-07-21	2002-12-10	Boehringer Ingelheim Pharmaceuticals, Inc.	Small molecules useful in the treatment of inflammatory disease
WO2002012243A2 (en) *	2000-08-09	2002-02-14	Boehringer Ingelheim Pharmaceuticals, Inc.	SYNTHESIS OF (R)-3-(4-BROMOBENZYL)-1-(3,5-DICHLOROPHENYL)-5-IODO-3-METHYL-1-H-IMIDAZO[1,2-a]IMIDAZOL-2-ONE
US6696441B1 (en) *	2000-08-11	2004-02-24	The Regents Of The University Of California	Inhibition of p53-induced stress response
JP2004509863A (ja) *	2000-09-21	2004-04-02	ブリストル−マイヤーズ　スクイブ　カンパニー	コルチコトロピン放出因子のインヒビターとしての置換アゾール誘導体
KR20040034594A (ko) *	2001-01-26	2004-04-28	브리스톨-마이어스스퀴브컴파니	코르티코트로핀 방출 인자 억제제로서의 이미다졸릴 유도체

2002
- 2002-01-11 KR KR10-2003-7009883A patent/KR20040034594A/ko not_active Withdrawn
- 2002-01-11 BR BR0206698-0A patent/BR0206698A/pt not_active IP Right Cessation
- 2002-01-11 PL PL02368555A patent/PL368555A1/xx unknown
- 2002-01-11 CN CNA028071352A patent/CN1499972A/zh active Pending
- 2002-01-11 US US10/044,183 patent/US6888004B2/en not_active Expired - Lifetime
- 2002-01-11 IL IL15681302A patent/IL156813A0/xx unknown
- 2002-01-11 SK SK922-2003A patent/SK9222003A3/sk unknown
- 2002-01-11 EP EP02705754A patent/EP1359916A4/en not_active Withdrawn
- 2002-01-11 JP JP2002559038A patent/JP2004531475A/ja active Pending
- 2002-01-11 WO PCT/US2002/000841 patent/WO2002058704A1/en not_active Ceased
- 2002-01-11 CA CA002434558A patent/CA2434558A1/en not_active Abandoned
- 2002-01-11 HR HR20030675A patent/HRP20030675A2/hr not_active Application Discontinuation
- 2002-01-11 CZ CZ20032044A patent/CZ20032044A3/cs unknown
- 2002-01-11 RU RU2003126188/04A patent/RU2003126188A/ru not_active Application Discontinuation
- 2002-01-11 EE EEP200300342A patent/EE200300342A/xx unknown
- 2002-01-11 MX MXPA03006484A patent/MXPA03006484A/es unknown
- 2002-01-11 HU HU0303721A patent/HUP0303721A2/hu unknown
- 2002-01-25 PE PE2002000063A patent/PE20020844A1/es not_active Application Discontinuation
2003
- 2003-07-17 ZA ZA200305531A patent/ZA200305531B/en unknown
- 2003-07-17 BG BG107999A patent/BG107999A/xx unknown
- 2003-07-24 IS IS6889A patent/IS6889A/is unknown
- 2003-07-25 NO NO20033350A patent/NO20033350L/no not_active Application Discontinuation
2004
- 2004-01-29 US US10/767,645 patent/US7211669B2/en not_active Expired - Lifetime
- 2004-02-04 US US10/772,027 patent/US7244746B2/en not_active Expired - Lifetime
- 2004-02-04 US US10/771,766 patent/US7238699B2/en not_active Expired - Lifetime
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Also Published As

Publication number	Publication date
RU2003126188A (ru)	2005-03-27
BR0206698A (pt)	2004-04-20
EP1359916A1 (en)	2003-11-12
US20040254382A1 (en)	2004-12-16
NO20033350D0 (no)	2003-07-25
IS6889A (is)	2003-07-24
US20040225130A1 (en)	2004-11-11
US20020183375A1 (en)	2002-12-05
CZ20032044A3 (cs)	2003-12-17
US7244746B2 (en)	2007-07-17
PL368555A1 (en)	2005-04-04
CN1499972A (zh)	2004-05-26
US20040235924A1 (en)	2004-11-25
HUP0303721A2 (hu)	2004-03-01
PE20020844A1 (es)	2002-09-27
NO20033350L (no)	2003-09-22
US6888004B2 (en)	2005-05-03
US20040225001A1 (en)	2004-11-11
WO2002058704A1 (en)	2002-08-01
US7211669B2 (en)	2007-05-01
US7238699B2 (en)	2007-07-03
US7125990B2 (en)	2006-10-24
IL156813A0 (en)	2004-02-08
KR20040034594A (ko)	2004-04-28
MXPA03006484A (es)	2003-09-22
JP2004531475A (ja)	2004-10-14
ZA200305531B (en)	2004-07-27
CA2434558A1 (en)	2002-08-01
HRP20030675A2 (en)	2004-08-31
EE200300342A (et)	2003-12-15
BG107999A (en)	2004-08-31
EP1359916A4 (en)	2004-04-07

Publication	Publication Date	Title
SK9222003A3 (en)	2004-05-04	Imidazolyl derivatives as corticotropin releasing factor inhibitors
KR100225720B1 (ko)	1999-10-15	부신피질자극호르몬-방출 인자 길항제로서의 피라졸로피리미딘을 포함하는 약학 조성물
KR100767272B1 (ko)	2007-10-17	Ｃｒｆ 활성을 갖는 융합 피리미딘 유도체
AU2002248151B2 (en)	2008-02-21	Compounds specific to adenosine A1, A2A, and A3 receptor and uses thereof
US7109193B2 (en)	2006-09-19	Tricyclic diazepines tocolytic oxytocin receptor antagonists
AU2010292487A1 (en)	2012-03-22	Heterocyclic compounds as janus kinase inhibitors
BG106568A (bg)	2002-12-29	5-(2-заместени-5-хетероциклилсулфонилпирид-3-ил)-дихидропиразоло[4,3-d]пиримидин-7-они като фосфодиестеразни инхибитори
CZ302486B6 (cs)	2011-06-15	N-6-Substituovaný 7-deazapurin, zpusob jeho prípravy a farmaceutická kompozice s jeho obsahem
US4873244A (en)	1989-10-10	Tricyclic heterocyclic compounds as psychopharmaceuticals
US7064120B2 (en)	2006-06-20	Tricyclic pyridyl carboxamides and derivatives thereof tocolytic oxytocin receptor antagonists
BRPI0616767A2 (pt)	2011-06-28	derivados de pirazolo [1,5-alfa]pirimidinila úteis como antagonistas de receptores de fatores de liberação de corticotropina (crf), composição contendo tais compostos, bem como usos
JP2002543199A (ja)	2002-12-17	ホスホジエステラーゼＩＶを阻害する１−アミノトリアゾロ［４，３−ａ］キナゾリン−５−オン、および／または−５−チオン
US20020147338A1 (en)	2002-10-10	Pyrazolotriazines as CRF antagonists
MXPA03009336A (es)	2004-11-12	Nuevas hidroxi ciclohexenil fenil carboxamidas como antagonistas del receptor de oxitocina tocoliticos.
US6903087B2 (en)	2005-06-07	Pyrido cyclohexenyl phenyl carboxamides tocolytic oxytocin receptor antagonists
AU2011299936A1 (en)	2013-03-28	Quinoxaline compound
AU2002239884A1 (en)	2002-08-06	Imidazolyl derivatives as corticotropin releasing factor inhibitors
NO177749B (no)	1995-08-07	Analogifremgangsmåte ved fremstilling av 2,4,8-tri-substituerte 3H,6H-1,4,5a,8a-tetraazaace-naftylen-3,5-(4H)-dioner
MXPA00009575A (en)	2001-07-31	Aminoalkyl substituted pyrrolo[2,3-b]pyridine and pyrrolo[2,3-d]pyrimidine derivatives:modulators of crf1 receptors