IL176765A - Inhibitors of glutaminyl cyclase - Google Patents

Inhibitors of glutaminyl cyclase

Info

Publication number: IL176765A
Authority: IL; Israel
Prior art keywords: phenyl; inhibitors; formula; inhibitor; compound
Prior art date: 2004-02-05

Application number

IL176765A

Other languages

English (en)

Other versions

IL176765A0 (en

Original Assignee

Probiodrug Ag

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.)

2004-02-05

Filing date

2006-07-10

Publication date

2011-08-31

2004-05-05 Priority claimed from US10/838,993 external-priority patent/US7371871B2/en

2005-02-04 Priority claimed from PCT/EP2005/001153 external-priority patent/WO2005075436A2/en

2006-07-10 Application filed by Probiodrug Ag filed Critical Probiodrug Ag

2006-10-31 Publication of IL176765A0 publication Critical patent/IL176765A0/en

2011-08-31 Publication of IL176765A publication Critical patent/IL176765A/en

Links

239000003112 inhibitor Substances 0.000 title claims description 175
108010081484 glutaminyl-peptide cyclotransferase Proteins 0.000 title claims description 29
102000003642 glutaminyl-peptide cyclotransferase Human genes 0.000 title claims description 29
-1 dihydrobenzodithiine Chemical compound 0.000 claims description 222
150000001875 compounds Chemical class 0.000 claims description 173
108090000765 processed proteins & peptides Proteins 0.000 claims description 84
125000000217 alkyl group Chemical group 0.000 claims description 57
102000004190 Enzymes Human genes 0.000 claims description 52
108090000790 Enzymes Proteins 0.000 claims description 52
230000001771 impaired effect Effects 0.000 claims description 45
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 34
150000003839 salts Chemical class 0.000 claims description 32
239000008194 pharmaceutical composition Substances 0.000 claims description 29
230000033228 biological regulation Effects 0.000 claims description 24
102000004196 processed proteins & peptides Human genes 0.000 claims description 24
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
208000035475 disorder Diseases 0.000 claims description 19
125000000174 L-prolyl group Chemical class [H]N1C([H])([H])C([H])([H])C([H])([H])[C@@]1([H])C(*)=O 0.000 claims description 18
108010016626 Dipeptides Proteins 0.000 claims description 17
239000003814 drug Substances 0.000 claims description 17
238000002360 preparation method Methods 0.000 claims description 17
201000010099 disease Diseases 0.000 claims description 14
239000003446 ligand Substances 0.000 claims description 14
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
230000001537 neural effect Effects 0.000 claims description 14
229910052717 sulfur Inorganic materials 0.000 claims description 14
208000024827 Alzheimer disease Diseases 0.000 claims description 13
125000003545 alkoxy group Chemical group 0.000 claims description 13
229960002429 proline Drugs 0.000 claims description 13
229910052739 hydrogen Inorganic materials 0.000 claims description 12
201000010374 Down Syndrome Diseases 0.000 claims description 11
230000002860 competitive effect Effects 0.000 claims description 11
230000003284 homeostatic effect Effects 0.000 claims description 11
101000930822 Giardia intestinalis Dipeptidyl-peptidase 4 Proteins 0.000 claims description 10
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210000001124 body fluid Anatomy 0.000 claims description 10
239000010839 body fluid Substances 0.000 claims description 10
230000037149 energy metabolism Effects 0.000 claims description 10
230000037406 food intake Effects 0.000 claims description 10
235000012631 food intake Nutrition 0.000 claims description 10
229910052736 halogen Inorganic materials 0.000 claims description 10
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150000002367 halogens Chemical class 0.000 claims description 9
235000013930 proline Nutrition 0.000 claims description 9
201000000980 schizophrenia Diseases 0.000 claims description 9
208000007848 Alcoholism Diseases 0.000 claims description 8
102000002659 Amyloid Precursor Protein Secretases Human genes 0.000 claims description 8
208000019901 Anxiety disease Diseases 0.000 claims description 8
206010010904 Convulsion Diseases 0.000 claims description 8
206010012289 Dementia Diseases 0.000 claims description 8
206010020772 Hypertension Diseases 0.000 claims description 8
208000028017 Psychotic disease Diseases 0.000 claims description 8
206010037660 Pyrexia Diseases 0.000 claims description 8
208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims description 8
201000007930 alcohol dependence Diseases 0.000 claims description 8
208000022531 anorexia Diseases 0.000 claims description 8
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108091007739 gamma-secretases Proteins 0.000 claims description 8
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239000003395 histamine H3 receptor antagonist Substances 0.000 claims description 8
208000015122 neurodegenerative disease Diseases 0.000 claims description 8
230000001717 pathogenic effect Effects 0.000 claims description 8
125000006413 ring segment Chemical group 0.000 claims description 8
238000006467 substitution reaction Methods 0.000 claims description 8
229940123320 Cyclase inhibitor Drugs 0.000 claims description 7
239000000556 agonist Substances 0.000 claims description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
230000008021 deposition Effects 0.000 claims description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
239000002899 monoamine oxidase inhibitor Substances 0.000 claims description 7
102000009091 Amyloidogenic Proteins Human genes 0.000 claims description 6
108010048112 Amyloidogenic Proteins Proteins 0.000 claims description 6
102000003729 Neprilysin Human genes 0.000 claims description 6
108090000028 Neprilysin Proteins 0.000 claims description 6
102100028656 Sigma non-opioid intracellular receptor 1 Human genes 0.000 claims description 6
101710104750 Sigma non-opioid intracellular receptor 1 Proteins 0.000 claims description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
239000002452 tumor necrosis factor alpha inhibitor Substances 0.000 claims description 6
229940046728 tumor necrosis factor alpha inhibitor Drugs 0.000 claims description 6
229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 claims description 5
229940082992 antihypertensives mao inhibitors Drugs 0.000 claims description 5
125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 5
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
239000000546 pharmaceutical excipient Substances 0.000 claims description 5
239000002587 phosphodiesterase IV inhibitor Substances 0.000 claims description 5
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 claims description 4
125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 claims description 4
125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 4
125000004060 L-alloisoleucine group Chemical group [H]N([H])[C@]([H])(C(=O)[*])[C@@](C([H])([H])[H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 4
125000003277 amino group Chemical group 0.000 claims description 4
210000004899 c-terminal region Anatomy 0.000 claims description 4
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 4
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
239000000126 substance Substances 0.000 claims description 4
ORZXYSPOAVJYRU-HOTGVXAUSA-N z-pro-prolinal Chemical compound O=C[C@@H]1CCCN1C(=O)[C@H]1N(C(=O)OCC=2C=CC=CC=2)CCC1 ORZXYSPOAVJYRU-HOTGVXAUSA-N 0.000 claims description 4
ZOLNSECVOZFNLU-UHFFFAOYSA-N 3h-1,2-benzoxathiole Chemical compound C1=CC=C2CSOC2=C1 ZOLNSECVOZFNLU-UHFFFAOYSA-N 0.000 claims description 3
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
150000002576 ketones Chemical class 0.000 claims description 3
125000001500 prolyl group Chemical group [H]N1C([H])(C(=O)[*])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
XGNBIYXILDDDQR-DTWKUNHWSA-N (2s)-1-[(2s)-2-amino-3,3-dimethylbutanoyl]pyrrolidine-2-carbonitrile Chemical compound CC(C)(C)[C@H](N)C(=O)N1CCC[C@H]1C#N XGNBIYXILDDDQR-DTWKUNHWSA-N 0.000 claims description 2
SUNMBRGCANLOEG-UHFFFAOYSA-N 1,3-dichloroacetone Chemical class ClCC(=O)CCl SUNMBRGCANLOEG-UHFFFAOYSA-N 0.000 claims description 2
AGRIQBHIKABLPJ-UHFFFAOYSA-N 1-Pyrrolidinecarboxaldehyde Chemical compound O=CN1CCCC1 AGRIQBHIKABLPJ-UHFFFAOYSA-N 0.000 claims description 2
WHGMHGPIJZTKTI-UHFFFAOYSA-N 3h-1,2-benzodithiole Chemical compound C1=CC=C2CSSC2=C1 WHGMHGPIJZTKTI-UHFFFAOYSA-N 0.000 claims description 2
125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 2
125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
QSAIYEIQUKKBDM-VYRBHSGPSA-N 9H-fluoren-9-ylmethyl N-[(2S)-1-(2-cyanopyrrolidin-1-yl)-1-oxopropan-2-yl]carbamate Chemical group C1=CC=CC=2C3=CC=CC=C3C(C1=2)COC(=O)N[C@@H](C)C(=O)N1C(CCC1)C#N QSAIYEIQUKKBDM-VYRBHSGPSA-N 0.000 claims description 2
229940125373 Gamma-Secretase Inhibitor Drugs 0.000 claims description 2
ULEBESPCVWBNIF-BYPYZUCNSA-N L-arginine amide Chemical compound NC(=O)[C@@H](N)CCCNC(N)=N ULEBESPCVWBNIF-BYPYZUCNSA-N 0.000 claims description 2
229930182821 L-proline Natural products 0.000 claims description 2
LHXOCOHMBFOVJS-OAHLLOKOSA-N Ladostigil Chemical group CCN(C)C(=O)OC1=CC=C2CC[C@@H](NCC#C)C2=C1 LHXOCOHMBFOVJS-OAHLLOKOSA-N 0.000 claims description 2
125000001931 aliphatic group Chemical group 0.000 claims description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
239000003540 gamma secretase inhibitor Substances 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
229950008812 ladostigil Drugs 0.000 claims description 2
GSYSFVSGPABNNL-UHFFFAOYSA-N methyl 2-dimethoxyphosphoryl-2-(phenylmethoxycarbonylamino)acetate Chemical group COC(=O)C(P(=O)(OC)OC)NC(=O)OCC1=CC=CC=C1 GSYSFVSGPABNNL-UHFFFAOYSA-N 0.000 claims description 2
150000003147 proline derivatives Chemical class 0.000 claims description 2
HDLWINONZUFKQV-QMMMGPOBSA-N pyrrolidin-1-yl-[(2s)-pyrrolidin-2-yl]methanone Chemical class C1CCCN1C(=O)[C@@H]1CCCN1 HDLWINONZUFKQV-QMMMGPOBSA-N 0.000 claims description 2
HJORMJIFDVBMOB-UHFFFAOYSA-N rolipram Chemical compound COC1=CC=C(C2CC(=O)NC2)C=C1OC1CCCC1 HJORMJIFDVBMOB-UHFFFAOYSA-N 0.000 claims description 2
229950005741 rolipram Drugs 0.000 claims description 2
SYOKIDBDQMKNDQ-XWTIBIIYSA-N vildagliptin Chemical compound C1C(O)(C2)CC(C3)CC1CC32NCC(=O)N1CCC[C@H]1C#N SYOKIDBDQMKNDQ-XWTIBIIYSA-N 0.000 claims description 2
229910052799 carbon Inorganic materials 0.000 claims 3
150000001721 carbon Chemical group 0.000 claims 3
125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims 2
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 2
125000006306 4-iodophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1I 0.000 claims 2
102100031674 Protein-L-isoaspartate(D-aspartate) O-methyltransferase Human genes 0.000 claims 2
108010018276 trimethylguanosine synthase Proteins 0.000 claims 2
CYDZCFWTMBKLOW-ZDUSSCGKSA-N (2s)-1-[4-[(4-chlorophenyl)methylamino]-4-oxobutanoyl]pyrrolidine-2-carboxylic acid Chemical compound OC(=O)[C@@H]1CCCN1C(=O)CCC(=O)NCC1=CC=C(Cl)C=C1 CYDZCFWTMBKLOW-ZDUSSCGKSA-N 0.000 claims 1
RICKQPKTSOSCOF-HKUYNNGSSA-N (3s)-2-[(2s)-2-amino-3-(1h-indol-3-yl)propanoyl]-3,4-dihydro-1h-isoquinoline-3-carboxylic acid Chemical compound C1C2=CC=CC=C2C[C@@H](C(O)=O)N1C(=O)[C@@H](N)CC1=CNC2=CC=CC=C12 RICKQPKTSOSCOF-HKUYNNGSSA-N 0.000 claims 1
GWHQHAUAXRMMOT-MERQFXBCSA-N 2,3-dihydroxybutanedioic acid;[3-[(1s)-1-(dimethylamino)ethyl]phenyl] n-ethyl-n-methylcarbamate Chemical group OC(=O)C(O)C(O)C(O)=O.CCN(C)C(=O)OC1=CC=CC([C@H](C)N(C)C)=C1 GWHQHAUAXRMMOT-MERQFXBCSA-N 0.000 claims 1
GRUVVLWKPGIYEG-UHFFFAOYSA-N 2-[2-[carboxymethyl-[(2-hydroxyphenyl)methyl]amino]ethyl-[(2-hydroxyphenyl)methyl]amino]acetic acid Chemical compound C=1C=CC=C(O)C=1CN(CC(=O)O)CCN(CC(O)=O)CC1=CC=CC=C1O GRUVVLWKPGIYEG-UHFFFAOYSA-N 0.000 claims 1
IHBAVXVTGLANPI-QMMMGPOBSA-N 2-amino-3-methyl-1-pyrrolidin-1-yl-butan-1-one Chemical compound CC(C)[C@H](N)C(=O)N1CCCC1 IHBAVXVTGLANPI-QMMMGPOBSA-N 0.000 claims 1
LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 claims 1
FEWJPZIEWOKRBE-JCYAYHJZSA-M L-tartrate(1-) Chemical compound OC(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-M 0.000 claims 1
XSVMFMHYUFZWBK-NSHDSACASA-N Rivastigmine Chemical compound CCN(C)C(=O)OC1=CC=CC([C@H](C)N(C)C)=C1 XSVMFMHYUFZWBK-NSHDSACASA-N 0.000 claims 1
RUOGJYKOQBFJIG-UHFFFAOYSA-N SCH-351591 Chemical compound C12=CC=C(C(F)(F)F)N=C2C(OC)=CC=C1C(=O)NC1=C(Cl)C=[N+]([O-])C=C1Cl RUOGJYKOQBFJIG-UHFFFAOYSA-N 0.000 claims 1
ZSBOMTDTBDDKMP-OAHLLOKOSA-N alogliptin Chemical compound C=1C=CC=C(C#N)C=1CN1C(=O)N(C)C(=O)C=C1N1CCC[C@@H](N)C1 ZSBOMTDTBDDKMP-OAHLLOKOSA-N 0.000 claims 1
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WROHEWWOCPRMIA-UHFFFAOYSA-N gsk-189,254 Chemical compound N1=CC(C(=O)NC)=CC=C1OC1=CC=C(CCN(CC2)C3CCC3)C2=C1 WROHEWWOCPRMIA-UHFFFAOYSA-N 0.000 claims 1
150000002431 hydrogen Chemical class 0.000 claims 1
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ATYBXHSAIOKLMG-UHFFFAOYSA-N oxepin Chemical compound O1C=CC=CC=C1 ATYBXHSAIOKLMG-UHFFFAOYSA-N 0.000 claims 1
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CSOBIBXVIYAXFM-UHFFFAOYSA-N rpl-554 Chemical compound C1=2C=C(OC)C(OC)=CC=2CCN(C(N2CCNC(N)=O)=O)C1=CC2=NC1=C(C)C=C(C)C=C1C CSOBIBXVIYAXFM-UHFFFAOYSA-N 0.000 claims 1
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IL176765A 2004-02-05 2006-07-10 Inhibitors of glutaminyl cyclase IL176765A (en)

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US54213304P	2004-02-05	2004-02-05
US10/838,993 US7371871B2 (en)	2003-05-05	2004-05-05	Inhibitors of glutaminyl cyclase
US63436404P	2004-12-08	2004-12-08
PCT/EP2005/001153 WO2005075436A2 (en)	2004-02-05	2005-02-04	Novel inhibitors of glutaminyl cyclase

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HUP0302962A2 (hu) *	1998-06-12	2003-12-29	Societe De Conseils De Recherches Et D'applications Scientifiques S.A.S.	Béta-karbolinszármazékok, ezeket a vegyületeket tartalmazó gyógyászati készítmények és a vegyületek alkalmazása
CA2417507A1 (en) *	2000-08-21	2002-02-28	Pacific Corporation	Novel thiourea derivatives and the pharmaceutical compositions containing the same
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DK1713780T3 (da)	2012-05-07
ATE541835T1 (de)	2012-02-15
IL176765A0 (en)	2006-10-31
EA013790B1 (ru)	2010-06-30
EA200601411A1 (ru)	2007-02-27

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Publication	Publication Date	Title
US7304086B2 (en)	2007-12-04	Inhibitors of glutaminyl cyclase
US7371871B2 (en)	2008-05-13	Inhibitors of glutaminyl cyclase
US7732162B2 (en)	2010-06-08	Inhibitors of glutaminyl cyclase for treating neurodegenerative diseases
CA2735795C (en)	2018-02-20	Novel inhibitors
DK2686313T3 (en)	2016-05-02	Benzimidazole derivatives as inhibitors of glutaminyl cyclase
KR20190136005A (ko)	2019-12-09	신규한 억제제
NZ546887A (en)	2009-04-30	Combinations useful for the treatment of neuronal disorders
IL176765A (en)	2011-08-31	Inhibitors of glutaminyl cyclase
NZ548596A (en)	2009-11-27	Novel inhibitors of glutaminyl cyclase and their use in treating neuronal diseases
EVANS	2005	Schilling et al.(43) Pub. Date: Sep. 29, 2005
MXPA06008868A (en)	2007-04-10	Novel inhibitors of glutaminyl cyclase
CENTER	0	Schilling et al.(43) Pub. Date: Nov. 11, 2004
HK1100943B (en)	2011-11-25	Inhibitors of glutaminyl cyclase
ES2348500T3 (es)	2010-12-07	Uso medico de inhibidores de glutaminil y glutamato ciclasas para el tratamiento de la enfermedad de alzheimer y el sindrome de down.
HK1178528B (en)	2016-11-18	Heterocyclic inhibitors of glutaminyl cyclase (qc, ec 2.3.2.5)
HK1178528A1 (zh)	2013-09-13	谷氨酰胺酰环化酶(qc，ec 2．3．2．5)的杂环抑制剂