IL144238A - 2 - Aryl - 3 - (Troeril) - Imadazo [2,1-a] Pyrimidines are converted in position 7, their preparation and pharmaceutical preparations containing them - Google Patents

2 - Aryl - 3 - (Troeril) - Imadazo [2,1-a] Pyrimidines are converted in position 7, their preparation and pharmaceutical preparations containing them

Info

Publication number: IL144238A
Authority: IL; Israel
Prior art keywords: compound; amine; pyrimidin; imidazo; formula
Prior art date: 1999-11-10

Application number

IL144238A

Other languages

English (en)

Hebrew (he)

Original Assignee

Ortho Mcneil Pharm Inc

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.)

1999-11-10

Filing date

2001-07-10

Publication date

2007-03-08

2001-07-10 Application filed by Ortho Mcneil Pharm Inc filed Critical Ortho Mcneil Pharm Inc

2007-03-08 Publication of IL144238A publication Critical patent/IL144238A/en

Links

239000008194 pharmaceutical composition Substances 0.000 title claims description 17
238000002360 preparation method Methods 0.000 title description 6
150000001875 compounds Chemical class 0.000 claims description 118
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 37
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 27
-1 C^alkoxy Chemical group 0.000 claims description 23
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 23
WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 21
229910052736 halogen Inorganic materials 0.000 claims description 17
150000002367 halogens Chemical class 0.000 claims description 17
238000004519 manufacturing process Methods 0.000 claims description 17
238000000034 method Methods 0.000 claims description 17
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
102000004127 Cytokines Human genes 0.000 claims description 14
108090000695 Cytokines Proteins 0.000 claims description 14
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
125000000623 heterocyclic group Chemical group 0.000 claims description 12
230000002757 inflammatory effect Effects 0.000 claims description 12
230000001404 mediated effect Effects 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 8
206010039073 rheumatoid arthritis Diseases 0.000 claims description 8
WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 claims description 8
230000009471 action Effects 0.000 claims description 7
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
239000003937 drug carrier Substances 0.000 claims description 7
BOJQXJHNUIWISM-UHFFFAOYSA-N imidazo[1,2-a]pyrimidin-7-amine Chemical compound N1=C(N)C=CN2C=CN=C21 BOJQXJHNUIWISM-UHFFFAOYSA-N 0.000 claims description 7
230000002401 inhibitory effect Effects 0.000 claims description 7
230000008569 process Effects 0.000 claims description 7
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
230000009467 reduction Effects 0.000 claims description 6
150000003839 salts Chemical class 0.000 claims description 6
125000003118 aryl group Chemical group 0.000 claims description 5
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 4
125000004076 pyridyl group Chemical group 0.000 claims description 4
125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 4
208000022559 Inflammatory bowel disease Diseases 0.000 claims description 3
208000001132 Osteoporosis Diseases 0.000 claims description 3
206010040070 Septic Shock Diseases 0.000 claims description 3
210000001744 T-lymphocyte Anatomy 0.000 claims description 3
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 3
201000008482 osteoarthritis Diseases 0.000 claims description 3
230000036303 septic shock Effects 0.000 claims description 3
YQSFQNMEKQXOET-UHFFFAOYSA-N 2-(3-fluorophenyl)-3-pyridin-4-ylimidazo[1,2-a]pyrimidin-7-amine Chemical compound N1=C2N=C(N)C=CN2C(C=2C=CN=CC=2)=C1C1=CC=CC(F)=C1 YQSFQNMEKQXOET-UHFFFAOYSA-N 0.000 claims description 2
YGBTVRUWFYRCNE-UHFFFAOYSA-N 3-(2-methoxypyrimidin-4-yl)-2-phenylimidazo[1,2-a]pyrimidin-7-amine Chemical compound COC1=NC=CC(C=2N3C=CC(N)=NC3=NC=2C=2C=CC=CC=2)=N1 YGBTVRUWFYRCNE-UHFFFAOYSA-N 0.000 claims description 2
KKPXTSJLILQNDB-UHFFFAOYSA-N 3-[2-(benzylamino)pyridin-4-yl]-2-[3-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrimidin-7-amine Chemical compound N1=C2N=C(N)C=CN2C(C=2C=C(NCC=3C=CC=CC=3)N=CC=2)=C1C1=CC=CC(C(F)(F)F)=C1 KKPXTSJLILQNDB-UHFFFAOYSA-N 0.000 claims description 2
INWFAMVJSJKINH-UHFFFAOYSA-N 3-pyridin-4-yl-2-[3-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrimidin-7-amine Chemical compound N1=C2N=C(N)C=CN2C(C=2C=CN=CC=2)=C1C1=CC=CC(C(F)(F)F)=C1 INWFAMVJSJKINH-UHFFFAOYSA-N 0.000 claims description 2
208000030507 AIDS Diseases 0.000 claims description 2
201000004384 Alopecia Diseases 0.000 claims description 2
208000024827 Alzheimer disease Diseases 0.000 claims description 2
201000001320 Atherosclerosis Diseases 0.000 claims description 2
206010006895 Cachexia Diseases 0.000 claims description 2
206010007559 Cardiac failure congestive Diseases 0.000 claims description 2
208000011231 Crohn disease Diseases 0.000 claims description 2
206010012289 Dementia Diseases 0.000 claims description 2
208000035895 Guillain-Barré syndrome Diseases 0.000 claims description 2
208000031886 HIV Infections Diseases 0.000 claims description 2
208000037357 HIV infectious disease Diseases 0.000 claims description 2
206010019280 Heart failures Diseases 0.000 claims description 2
206010049567 Miller Fisher syndrome Diseases 0.000 claims description 2
206010033645 Pancreatitis Diseases 0.000 claims description 2
206010033647 Pancreatitis acute Diseases 0.000 claims description 2
201000004681 Psoriasis Diseases 0.000 claims description 2
208000006011 Stroke Diseases 0.000 claims description 2
206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 2
201000003229 acute pancreatitis Diseases 0.000 claims description 2
230000009285 allergic inflammation Effects 0.000 claims description 2
231100000360 alopecia Toxicity 0.000 claims description 2
208000005017 glioblastoma Diseases 0.000 claims description 2
208000006454 hepatitis Diseases 0.000 claims description 2
231100000283 hepatitis Toxicity 0.000 claims description 2
208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 claims description 2
208000028867 ischemia Diseases 0.000 claims description 2
210000004072 lung Anatomy 0.000 claims description 2
201000006417 multiple sclerosis Diseases 0.000 claims description 2
208000004296 neuralgia Diseases 0.000 claims description 2
208000021722 neuropathic pain Diseases 0.000 claims description 2
208000028169 periodontal disease Diseases 0.000 claims description 2
208000005069 pulmonary fibrosis Diseases 0.000 claims description 2
230000010076 replication Effects 0.000 claims description 2
208000037803 restenosis Diseases 0.000 claims description 2
201000000596 systemic lupus erythematosus Diseases 0.000 claims description 2
208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 2
206010047470 viral myocarditis Diseases 0.000 claims description 2
JNPGUXGVLNJQSQ-BGGMYYEUSA-M (e,3r,5s)-7-[4-(4-fluorophenyl)-1,2-di(propan-2-yl)pyrrol-3-yl]-3,5-dihydroxyhept-6-enoate Chemical compound CC(C)N1C(C(C)C)=C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)C(C=2C=CC(F)=CC=2)=C1 JNPGUXGVLNJQSQ-BGGMYYEUSA-M 0.000 claims 4
QRDAPCMJAOQZSU-KQQUZDAGSA-N (e)-3-[4-[(e)-3-(3-fluorophenyl)-3-oxoprop-1-enyl]-1-methylpyrrol-2-yl]-n-hydroxyprop-2-enamide Chemical compound C1=C(\C=C\C(=O)NO)N(C)C=C1\C=C\C(=O)C1=CC=CC(F)=C1 QRDAPCMJAOQZSU-KQQUZDAGSA-N 0.000 claims 3
PHDIJLFSKNMCMI-ITGJKDDRSA-N (3R,4S,5R,6R)-6-(hydroxymethyl)-4-(8-quinolin-6-yloxyoctoxy)oxane-2,3,5-triol Chemical compound OC[C@@H]1[C@H]([C@@H]([C@H](C(O1)O)O)OCCCCCCCCOC=1C=C2C=CC=NC2=CC=1)O PHDIJLFSKNMCMI-ITGJKDDRSA-N 0.000 claims 2
HIHOEGPXVVKJPP-JTQLQIEISA-N 5-fluoro-2-[[(1s)-1-(5-fluoropyridin-2-yl)ethyl]amino]-6-[(5-methyl-1h-pyrazol-3-yl)amino]pyridine-3-carbonitrile Chemical compound N([C@@H](C)C=1N=CC(F)=CC=1)C(C(=CC=1F)C#N)=NC=1NC=1C=C(C)NN=1 HIHOEGPXVVKJPP-JTQLQIEISA-N 0.000 claims 2
CYSWUSAYJNCAKA-FYJFLYSWSA-N ClC1=C(C=CC=2N=C(SC=21)OCC)OC1=CC=C(C=N1)/C=C/[C@H](C)NC(C)=O Chemical compound ClC1=C(C=CC=2N=C(SC=21)OCC)OC1=CC=C(C=N1)/C=C/[C@H](C)NC(C)=O CYSWUSAYJNCAKA-FYJFLYSWSA-N 0.000 claims 2
SRVFFFJZQVENJC-IHRRRGAJSA-N aloxistatin Chemical compound CCOC(=O)[C@H]1O[C@@H]1C(=O)N[C@@H](CC(C)C)C(=O)NCCC(C)C SRVFFFJZQVENJC-IHRRRGAJSA-N 0.000 claims 2
QAPTWHXHEYAIKG-RCOXNQKVSA-N n-[(1r,2s,5r)-5-(tert-butylamino)-2-[(3s)-2-oxo-3-[[6-(trifluoromethyl)quinazolin-4-yl]amino]pyrrolidin-1-yl]cyclohexyl]acetamide Chemical compound CC(=O)N[C@@H]1C[C@H](NC(C)(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(=CC=C3N=CN=2)C(F)(F)F)CC1 QAPTWHXHEYAIKG-RCOXNQKVSA-N 0.000 claims 2
HBENZIXOGRCSQN-VQWWACLZSA-N (1S,2S,6R,14R,15R,16R)-5-(cyclopropylmethyl)-16-[(2S)-2-hydroxy-3,3-dimethylpentan-2-yl]-15-methoxy-13-oxa-5-azahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8(20),9,11-trien-11-ol Chemical compound N1([C@@H]2CC=3C4=C(C(=CC=3)O)O[C@H]3[C@@]5(OC)CC[C@@]2([C@@]43CC1)C[C@@H]5[C@](C)(O)C(C)(C)CC)CC1CC1 HBENZIXOGRCSQN-VQWWACLZSA-N 0.000 claims 1
VPMIAOSOTOODMY-KJAPKAAFSA-N (4r)-6-[(e)-2-[6-tert-butyl-4-(4-fluorophenyl)-2-propan-2-ylpyridin-3-yl]ethenyl]-4-hydroxyoxan-2-one Chemical compound C([C@H](O)C1)C(=O)OC1/C=C/C=1C(C(C)C)=NC(C(C)(C)C)=CC=1C1=CC=C(F)C=C1 VPMIAOSOTOODMY-KJAPKAAFSA-N 0.000 claims 1
VAVHMEQFYYBAPR-ITWZMISCSA-N (e,3r,5s)-7-[4-(4-fluorophenyl)-1-phenyl-2-propan-2-ylpyrrol-3-yl]-3,5-dihydroxyhept-6-enoic acid Chemical compound CC(C)C1=C(\C=C\[C@@H](O)C[C@@H](O)CC(O)=O)C(C=2C=CC(F)=CC=2)=CN1C1=CC=CC=C1 VAVHMEQFYYBAPR-ITWZMISCSA-N 0.000 claims 1
MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 claims 1
KVSJCXDUYDCCHX-UHFFFAOYSA-N 2-(3-chlorophenyl)-3-pyridin-4-ylimidazo[1,2-a]pyrimidin-7-amine Chemical compound N1=C2N=C(N)C=CN2C(C=2C=CN=CC=2)=C1C1=CC=CC(Cl)=C1 KVSJCXDUYDCCHX-UHFFFAOYSA-N 0.000 claims 1
BVOXXCFSYHFTLW-UHFFFAOYSA-N 2-(4-fluorophenyl)-3-(2-methylsulfanylpyrimidin-4-yl)imidazo[1,2-a]pyrimidin-7-amine Chemical compound CSC1=NC=CC(C=2N3C=CC(N)=NC3=NC=2C=2C=CC(F)=CC=2)=N1 BVOXXCFSYHFTLW-UHFFFAOYSA-N 0.000 claims 1
RFKYUEFCPXYIHY-UHFFFAOYSA-N 2-(4-fluorophenyl)-3-pyrimidin-4-ylimidazo[1,2-a]pyrimidin-7-amine Chemical compound N1=C2N=C(N)C=CN2C(C=2N=CN=CC=2)=C1C1=CC=C(F)C=C1 RFKYUEFCPXYIHY-UHFFFAOYSA-N 0.000 claims 1
SXMGPKIFJDLHQD-UHFFFAOYSA-N 2-(4-fluorophenyl)-3-quinolin-4-ylimidazo[1,2-a]pyrimidin-7-amine Chemical compound N1=C2N=C(N)C=CN2C(C=2C3=CC=CC=C3N=CC=2)=C1C1=CC=C(F)C=C1 SXMGPKIFJDLHQD-UHFFFAOYSA-N 0.000 claims 1
OUYMDMNELLLCOG-UHFFFAOYSA-N 2-phenyl-3-(2-piperidin-1-ylpyrimidin-4-yl)imidazo[1,2-a]pyrimidin-7-amine Chemical compound N1=C2N=C(N)C=CN2C(C=2N=C(N=CC=2)N2CCCCC2)=C1C1=CC=CC=C1 OUYMDMNELLLCOG-UHFFFAOYSA-N 0.000 claims 1
KFEQXUZWOONGQK-INIZCTEOSA-N 2-phenyl-3-[2-[[(1s)-1-phenylethyl]amino]pyrimidin-4-yl]imidazo[1,2-a]pyrimidin-7-amine Chemical compound N([C@@H](C)C=1C=CC=CC=1)C(N=1)=NC=CC=1C(N1C=CC(N)=NC1=N1)=C1C1=CC=CC=C1 KFEQXUZWOONGQK-INIZCTEOSA-N 0.000 claims 1
DMGWRGHGUCYNLG-UHFFFAOYSA-N 3-(2-bromopyridin-4-yl)-2-(4-fluorophenyl)imidazo[1,2-a]pyrimidin-7-amine Chemical compound N1=C2N=C(N)C=CN2C(C=2C=C(Br)N=CC=2)=C1C1=CC=C(F)C=C1 DMGWRGHGUCYNLG-UHFFFAOYSA-N 0.000 claims 1
NQNOOPZIWTUKRT-HNNXBMFYSA-N 3-[2-[[(1s)-1-phenylethyl]amino]pyrimidin-4-yl]-2-[3-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrimidin-7-amine Chemical compound N([C@@H](C)C=1C=CC=CC=1)C(N=1)=NC=CC=1C(N1C=CC(N)=NC1=N1)=C1C1=CC=CC(C(F)(F)F)=C1 NQNOOPZIWTUKRT-HNNXBMFYSA-N 0.000 claims 1
YWQVMSDKUMRDSW-UHFFFAOYSA-N 3-pyrimidin-4-yl-2-[3-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrimidin-7-amine Chemical compound N1=C2N=C(N)C=CN2C(C=2N=CN=CC=2)=C1C1=CC=CC(C(F)(F)F)=C1 YWQVMSDKUMRDSW-UHFFFAOYSA-N 0.000 claims 1
REDUQXCPUSNJOL-UHFFFAOYSA-N C(C1=CC=CC=C1)NC(CN(C(C1=CC=C(C=C1)C(C)C)=O)CC1=CC=C(C=C1)C(NO)=O)=O Chemical compound C(C1=CC=CC=C1)NC(CN(C(C1=CC=C(C=C1)C(C)C)=O)CC1=CC=C(C=C1)C(NO)=O)=O REDUQXCPUSNJOL-UHFFFAOYSA-N 0.000 claims 1
QBXVXKRWOVBUDB-GRKNLSHJSA-N ClC=1C(=CC(=C(CN2[C@H](C[C@H](C2)O)C(=O)O)C1)OCC1=CC(=CC=C1)C#N)OCC1=C(C(=CC=C1)C1=CC2=C(OCCO2)C=C1)C Chemical compound ClC=1C(=CC(=C(CN2[C@H](C[C@H](C2)O)C(=O)O)C1)OCC1=CC(=CC=C1)C#N)OCC1=C(C(=CC=C1)C1=CC2=C(OCCO2)C=C1)C QBXVXKRWOVBUDB-GRKNLSHJSA-N 0.000 claims 1
102100025027 E3 ubiquitin-protein ligase TRIM69 Human genes 0.000 claims 1
101000830203 Homo sapiens E3 ubiquitin-protein ligase TRIM69 Proteins 0.000 claims 1
YLEIFZAVNWDOBM-ZTNXSLBXSA-N ac1l9hc7 Chemical compound C([C@H]12)C[C@@H](C([C@@H](O)CC3)(C)C)[C@@]43C[C@@]14CC[C@@]1(C)[C@@]2(C)C[C@@H]2O[C@]3(O)[C@H](O)C(C)(C)O[C@@H]3[C@@H](C)[C@H]12 YLEIFZAVNWDOBM-ZTNXSLBXSA-N 0.000 claims 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
GVOISEJVFFIGQE-YCZSINBZSA-N n-[(1r,2s,5r)-5-[methyl(propan-2-yl)amino]-2-[(3s)-2-oxo-3-[[6-(trifluoromethyl)quinazolin-4-yl]amino]pyrrolidin-1-yl]cyclohexyl]acetamide Chemical compound CC(=O)N[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(=CC=C3N=CN=2)C(F)(F)F)CC1 GVOISEJVFFIGQE-YCZSINBZSA-N 0.000 claims 1
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 1
125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 32
239000000243 solution Substances 0.000 description 30
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
108060008682 Tumor Necrosis Factor Proteins 0.000 description 17
102100040247 Tumor necrosis factor Human genes 0.000 description 17
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
238000006243 chemical reaction Methods 0.000 description 15
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 13
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238000003556 assay Methods 0.000 description 11
235000019439 ethyl acetate Nutrition 0.000 description 11
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
239000003921 oil Substances 0.000 description 10
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230000000694 effects Effects 0.000 description 8
239000002158 endotoxin Substances 0.000 description 8
229960000583 acetic acid Drugs 0.000 description 7
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 7
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
239000002904 solvent Substances 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 6
241001465754 Metazoa Species 0.000 description 6
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210000004027 cell Anatomy 0.000 description 6
239000012362 glacial acetic acid Substances 0.000 description 6
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238000012360 testing method Methods 0.000 description 6
AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 5
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GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 4
IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 4
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DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 1
OBRVWKVGULVSOR-UHFFFAOYSA-N tert-butyl 2-(benzylamino)-4-methyl-2h-pyridine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1C=CC(C)=CC1NCC1=CC=CC=C1 OBRVWKVGULVSOR-UHFFFAOYSA-N 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
230000006433 tumor necrosis factor production Effects 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
230000003612 virological effect Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000002699 waste material Substances 0.000 description 1
125000005023 xylyl group Chemical group 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
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- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
- A—HUMAN NECESSITIES
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- A61P1/18—Drugs for disorders of the alimentary tract or the digestive system for pancreatic disorders, e.g. pancreatic enzymes
- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P17/14—Drugs for dermatological disorders for baldness or alopecia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
- A—HUMAN NECESSITIES
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- A61P25/04—Centrally acting analgesics, e.g. opioids
- A—HUMAN NECESSITIES
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- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis

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Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
General Chemical & Material Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Immunology (AREA)
Rheumatology (AREA)
Physical Education & Sports Medicine (AREA)
Oncology (AREA)
Diabetes (AREA)
Orthopedic Medicine & Surgery (AREA)
Virology (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Communicable Diseases (AREA)
Pain & Pain Management (AREA)
Heart & Thoracic Surgery (AREA)
Dermatology (AREA)
Pulmonology (AREA)
Cardiology (AREA)
Obesity (AREA)
Hospice & Palliative Care (AREA)
Urology & Nephrology (AREA)
Molecular Biology (AREA)
Tropical Medicine & Parasitology (AREA)
Hematology (AREA)
Endocrinology (AREA)
Vascular Medicine (AREA)
Psychiatry (AREA)

IL144238A 1999-11-10 2001-07-10 2 - Aryl - 3 - (Troeril) - Imadazo [2,1-a] Pyrimidines are converted in position 7, their preparation and pharmaceutical preparations containing them IL144238A (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US16470099P	1999-11-10	1999-11-10
PCT/US2000/029875 WO2001034605A1 (en)	1999-11-10	2000-10-27	SUBSTITUTED 2-ARYL-3-(HETEROARYL)-IMIDAZO[1,2-a]PYRIMIDINES, AND RELATED PHARMACEUTICAL COMPOSITIONS AND METHODS
US09/698,448 US6610697B1 (en)	1999-11-10	2000-10-27	Substituted 2-aryl-3-(heteroaryl)-imidazo[1,2-a]pyrimidines, and related pharmaceutical compositions and methods

Publications (1)

Publication Number	Publication Date
IL144238A true IL144238A (en)	2007-03-08

Family

ID=22595694

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL144238A IL144238A (en)	1999-11-10	2001-07-10	2 - Aryl - 3 - (Troeril) - Imadazo [2,1-a] Pyrimidines are converted in position 7, their preparation and pharmaceutical preparations containing them

Country Status (27)

Country	Link
US (1)	US6610697B1 (de)
EP (1)	EP1140939B1 (de)
JP (1)	JP2003513977A (de)
KR (1)	KR20010089805A (de)
CN (1)	CN1255406C (de)
AR (1)	AR026410A1 (de)
AT (1)	ATE288915T1 (de)
AU (1)	AU784484B2 (de)
BG (1)	BG65106B1 (de)
BR (1)	BR0007447A (de)
CA (1)	CA2361139A1 (de)
CZ (1)	CZ20012494A3 (de)
DE (1)	DE60018037T2 (de)
ES (1)	ES2237470T3 (de)
HK (1)	HK1043591B (de)
HU (1)	HUP0200207A3 (de)
ID (1)	ID29514A (de)
IL (1)	IL144238A (de)
MX (1)	MXPA01007019A (de)
NO (1)	NO320422B1 (de)
NZ (1)	NZ512957A (de)
PL (1)	PL348924A1 (de)
PT (1)	PT1140939E (de)
RU (1)	RU2264403C2 (de)
SK (1)	SK9892001A3 (de)
UA (1)	UA70350C2 (de)
WO (1)	WO2001034605A1 (de)

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KR20080107408A (ko)	2006-03-07	2008-12-10	브리스톨-마이어스 스큅 컴퍼니	키나제 억제제로서 유용한 피롤로트리아진 아닐린 전구약물화합물
EP2057164A1 (de)	2006-08-07	2009-05-13	Incyte Corporation	Triazoltriazine als kinase-hemmer
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2000
- 2000-10-27 ES ES00976710T patent/ES2237470T3/es not_active Expired - Lifetime
- 2000-10-27 HK HK02105224.5A patent/HK1043591B/zh not_active IP Right Cessation
- 2000-10-27 NZ NZ512957A patent/NZ512957A/en unknown
- 2000-10-27 CZ CZ20012494A patent/CZ20012494A3/cs unknown
- 2000-10-27 PL PL00348924A patent/PL348924A1/xx not_active IP Right Cessation
- 2000-10-27 JP JP2001536552A patent/JP2003513977A/ja active Pending
- 2000-10-27 KR KR1020017008715A patent/KR20010089805A/ko not_active Ceased
- 2000-10-27 AT AT00976710T patent/ATE288915T1/de not_active IP Right Cessation
- 2000-10-27 WO PCT/US2000/029875 patent/WO2001034605A1/en not_active Ceased
- 2000-10-27 SK SK989-2001A patent/SK9892001A3/sk unknown
- 2000-10-27 US US09/698,448 patent/US6610697B1/en not_active Expired - Lifetime
- 2000-10-27 AU AU14445/01A patent/AU784484B2/en not_active Ceased
- 2000-10-27 ID IDW00200101720A patent/ID29514A/id unknown
- 2000-10-27 EP EP00976710A patent/EP1140939B1/de not_active Expired - Lifetime
- 2000-10-27 MX MXPA01007019A patent/MXPA01007019A/es active IP Right Grant
- 2000-10-27 UA UA2001075135A patent/UA70350C2/uk unknown
- 2000-10-27 RU RU2001122339/04A patent/RU2264403C2/ru not_active IP Right Cessation
- 2000-10-27 PT PT00976710T patent/PT1140939E/pt unknown
- 2000-10-27 DE DE60018037T patent/DE60018037T2/de not_active Expired - Fee Related
- 2000-10-27 CN CNB008045682A patent/CN1255406C/zh not_active Expired - Fee Related
- 2000-10-27 BR BR0007447-0A patent/BR0007447A/pt not_active IP Right Cessation
- 2000-10-27 CA CA002361139A patent/CA2361139A1/en not_active Abandoned
- 2000-10-27 HU HU0200207A patent/HUP0200207A3/hu unknown
- 2000-11-09 AR ARP000105910A patent/AR026410A1/es not_active Application Discontinuation
2001
- 2001-07-10 NO NO20013419A patent/NO320422B1/no not_active Application Discontinuation
- 2001-07-10 IL IL144238A patent/IL144238A/en not_active IP Right Cessation
- 2001-07-17 BG BG105712A patent/BG65106B1/bg unknown

Also Published As

Publication number	Publication date
AU1444501A (en)	2001-06-06
CN1342162A (zh)	2002-03-27
SK9892001A3 (en)	2002-04-04
RU2264403C2 (ru)	2005-11-20
BG105712A (en)	2002-06-28
HUP0200207A2 (hu)	2002-05-29
CN1255406C (zh)	2006-05-10
BR0007447A (pt)	2002-04-09
US6610697B1 (en)	2003-08-26
NO20013419D0 (no)	2001-07-10
ES2237470T3 (es)	2005-08-01
AU784484B2 (en)	2006-04-13
KR20010089805A (ko)	2001-10-08
ATE288915T1 (de)	2005-02-15
UA70350C2 (en)	2004-10-15
EP1140939A1 (de)	2001-10-10
CA2361139A1 (en)	2001-05-17
DE60018037D1 (de)	2005-03-17
DE60018037T2 (de)	2006-01-12
JP2003513977A (ja)	2003-04-15
NO20013419L (no)	2001-08-27
MXPA01007019A (es)	2002-09-18
HUP0200207A3 (en)	2004-07-28
NO320422B1 (no)	2005-12-05
AR026410A1 (es)	2003-02-12
CZ20012494A3 (cs)	2001-10-17
PL348924A1 (en)	2002-06-17
BG65106B1 (bg)	2007-02-28
ID29514A (id)	2001-09-06
HK1043591B (zh)	2006-12-29
NZ512957A (en)	2005-01-28
EP1140939B1 (de)	2005-02-09
PT1140939E (pt)	2005-05-31
HK1043591A1 (en)	2002-09-20
WO2001034605A1 (en)	2001-05-17

Legal Events

Date	Code	Title	Description
2011-06-30	MM9K	Patent not in force due to non-payment of renewal fees

Publication	Publication Date	Title
EP1140939B1 (de)	2005-02-09	Substituierte 2-aryl-3-(heteroaryl)-imidazo[1,2-alpha]pyrimidine und ihren verwandten arzneimittel und verfahren
US7026326B2 (en)	2006-04-11	Substituted heterocyclic compounds and methods of use
EP0994858A1 (de)	2000-04-26	Zur behandlung von entzündlichen krankheiten verwendbare 2-substituierte imidazole
AU2005319137B2 (en)	2009-01-08	Substituted heterocyclic compounds and methods of use
SK92898A3 (en)	1999-05-07	Novel substituted imidazole compounds
CZ392597A3 (cs)	1998-09-16	Imidazolové sloučeniny, způsob jejich přípravy, farmaceutické prostředky s jejich obsahem a způsob ošetřování
US7429594B2 (en)	2008-09-30	Substituted heterocyclic compounds and methods of use
EP1060181B1 (de)	2004-05-06	Substituierte pyrrolobenzimidazolderivate zur entzündungshemmung
AU777702B2 (en)	2004-10-28	Substituted 3-pyridyl-4-arylpyrroles, and related therapeutic and prophylactic methods
US20060247263A1 (en)	2006-11-02	Substituted heterocyclic compounds and methods of use
BG65128B1 (bg)	2007-03-30	Заместени пирамидинови съединения и тяхното използване
US7504403B2 (en)	2009-03-17	Substituted heterocyclic compounds and methods of use
BG63362B1 (bg)	2001-11-30	Нови заместени имидазоли