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

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2002
- 2002-01-11 KR KR10-2003-7009883A patent/KR20040034594A/ko not_active Withdrawn
- 2002-01-11 US US10/044,183 patent/US6888004B2/en not_active Expired - Lifetime
- 2002-01-11 EP EP02705754A patent/EP1359916A4/en not_active Withdrawn
- 2002-01-11 SK SK922-2003A patent/SK9222003A3/sk unknown
- 2002-01-11 JP JP2002559038A patent/JP2004531475A/ja active Pending
- 2002-01-11 IL IL15681302A patent/IL156813A0/xx unknown
- 2002-01-11 BR BR0206698-0A patent/BR0206698A/pt not_active IP Right Cessation
- 2002-01-11 WO PCT/US2002/000841 patent/WO2002058704A1/en not_active Ceased
- 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 CA CA002434558A patent/CA2434558A1/en not_active Abandoned
- 2002-01-11 CN CNA028071352A patent/CN1499972A/zh active Pending
- 2002-01-11 CZ CZ20032044A patent/CZ20032044A3/cs unknown
- 2002-01-11 HR HR20030675A patent/HRP20030675A2/hr not_active Application Discontinuation
- 2002-01-11 PL PL02368555A patent/PL368555A1/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 US10/771,661 patent/US7125990B2/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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Publication number	Publication date
US20040225001A1 (en)	2004-11-11
EE200300342A (et)	2003-12-15
KR20040034594A (ko)	2004-04-28
US7211669B2 (en)	2007-05-01
BG107999A (en)	2004-08-31
PE20020844A1 (es)	2002-09-27
US6888004B2 (en)	2005-05-03
US20040254382A1 (en)	2004-12-16
US7125990B2 (en)	2006-10-24
IL156813A0 (en)	2004-02-08
CA2434558A1 (en)	2002-08-01
HRP20030675A2 (en)	2004-08-31
PL368555A1 (en)	2005-04-04
IS6889A (is)	2003-07-24
EP1359916A4 (en)	2004-04-07
NO20033350L (no)	2003-09-22
NO20033350D0 (no)	2003-07-25
CZ20032044A3 (cs)	2003-12-17
WO2002058704A1 (en)	2002-08-01
US20040235924A1 (en)	2004-11-25
BR0206698A (pt)	2004-04-20
US7238699B2 (en)	2007-07-03
US20040225130A1 (en)	2004-11-11
HUP0303721A2 (hu)	2004-03-01
ZA200305531B (en)	2004-07-27
US20020183375A1 (en)	2002-12-05
EP1359916A1 (en)	2003-11-12
MXPA03006484A (es)	2003-09-22
US7244746B2 (en)	2007-07-17
JP2004531475A (ja)	2004-10-14
RU2003126188A (ru)	2005-03-27
CN1499972A (zh)	2004-05-26

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