DK3004079T3 - PYRIMIDE COMPOUNDS AND THEIR USE AS GAMMA SECRETASE MODULATORS - Google Patents

PYRIMIDE COMPOUNDS AND THEIR USE AS GAMMA SECRETASE MODULATORS Download PDF

Info

Publication number: DK3004079T3
Authority: DK; Denmark
Prior art keywords: methyl; methoxy; imidazol; trifluoroethoxy; mmol
Prior art date: 2013-06-04

Application number

DK14727562.2T

Other languages

Danish (da)

English (en)

Inventor

Yevgeni Besidski

Ulrika Yngve

Kim Paulsen

Christian Linde

István Macsári

Jonas Malmborg

Alexander Paptchikhine

Per Arvidsson

Original Assignee

Acturum Real Estate Ab

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.)

2013-06-04

Filing date

2014-06-03

Publication date

2018-04-16

2014-06-03 Application filed by Acturum Real Estate Ab filed Critical Acturum Real Estate Ab

2018-04-16 Application granted granted Critical

2018-04-16 Publication of DK3004079T3 publication Critical patent/DK3004079T3/en

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 286
VHNYOQKVZQVBLC-RTCGXNAVSA-N (4r,7e,9as)-7-[[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]methylidene]-4-(3,4,5-trifluorophenyl)-1,3,4,8,9,9a-hexahydropyrido[2,1-c][1,4]oxazin-6-one Chemical compound C1([C@@H]2COC[C@@H]3CC\C(C(N32)=O)=C/C=2C=C(C(=CC=2)N2C=C(C)N=C2)OC)=CC(F)=C(F)C(F)=C1 VHNYOQKVZQVBLC-RTCGXNAVSA-N 0.000 title 1
229940124648 γ-Secretase Modulator Drugs 0.000 title 1
150000003839 salts Chemical class 0.000 claims abstract description 40
238000011282 treatment Methods 0.000 claims abstract description 14
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 13
230000002265 prevention Effects 0.000 claims abstract description 9
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 8
201000010099 disease Diseases 0.000 claims abstract description 7
239000003814 drug Substances 0.000 claims abstract description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 291
-1 3-Methoxy -4- (4-methyl-1H-imidazol-1-yl) phenyl Chemical group 0.000 claims description 60
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 60
208000024827 Alzheimer disease Diseases 0.000 claims description 17
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
239000003795 chemical substances by application Substances 0.000 claims description 13
238000002560 therapeutic procedure Methods 0.000 claims description 13
ASUTZQLVASHGKV-JDFRZJQESA-N galanthamine Chemical compound O1C(=C23)C(OC)=CC=C2CN(C)CC[C@]23[C@@H]1C[C@@H](O)C=C2 ASUTZQLVASHGKV-JDFRZJQESA-N 0.000 claims description 12
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
KVWDHTXUZHCGIO-UHFFFAOYSA-N olanzapine Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2NC2=C1C=C(C)S2 KVWDHTXUZHCGIO-UHFFFAOYSA-N 0.000 claims description 10
206010012289 Dementia Diseases 0.000 claims description 8
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 8
239000003085 diluting agent Substances 0.000 claims description 8
239000003937 drug carrier Substances 0.000 claims description 8
229960005017 olanzapine Drugs 0.000 claims description 8
125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 8
239000000546 pharmaceutical excipient Substances 0.000 claims description 7
CEUORZQYGODEFX-UHFFFAOYSA-N Aripirazole Chemical compound ClC1=CC=CC(N2CCN(CCCCOC=3C=C4NC(=O)CCC4=CC=3)CC2)=C1Cl CEUORZQYGODEFX-UHFFFAOYSA-N 0.000 claims description 6
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 description 6
239000003693 atypical antipsychotic agent Substances 0.000 claims description 6
QZUDBNBUXVUHMW-UHFFFAOYSA-N clozapine Chemical compound C1CN(C)CCN1C1=NC2=CC(Cl)=CC=C2NC2=CC=CC=C12 QZUDBNBUXVUHMW-UHFFFAOYSA-N 0.000 claims description 6
229960004640 memantine Drugs 0.000 claims description 6
RAPZEAPATHNIPO-UHFFFAOYSA-N risperidone Chemical compound FC1=CC=C2C(C3CCN(CC3)CCC=3C(=O)N4CCCCC4=NC=3C)=NOC2=C1 RAPZEAPATHNIPO-UHFFFAOYSA-N 0.000 claims description 6
229960001685 tacrine Drugs 0.000 claims description 6
YLJREFDVOIBQDA-UHFFFAOYSA-N tacrine Chemical compound C1=CC=C2C(N)=C(CCCC3)C3=NC2=C1 YLJREFDVOIBQDA-UHFFFAOYSA-N 0.000 claims description 6
MVWVFYHBGMAFLY-UHFFFAOYSA-N ziprasidone Chemical compound C1=CC=C2C(N3CCN(CC3)CCC3=CC=4CC(=O)NC=4C=C3Cl)=NSC2=C1 MVWVFYHBGMAFLY-UHFFFAOYSA-N 0.000 claims description 6
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 5
229960004431 quetiapine Drugs 0.000 claims description 5
URKOMYMAXPYINW-UHFFFAOYSA-N quetiapine Chemical compound C1CN(CCOCCO)CCN1C1=NC2=CC=CC=C2SC2=CC=CC=C12 URKOMYMAXPYINW-UHFFFAOYSA-N 0.000 claims description 5
RTHCYVBBDHJXIQ-MRXNPFEDSA-N (R)-fluoxetine Chemical compound O([C@H](CCNC)C=1C=CC=CC=1)C1=CC=C(C(F)(F)F)C=C1 RTHCYVBBDHJXIQ-MRXNPFEDSA-N 0.000 claims description 4
IOBDVBVNPMCPMC-UHFFFAOYSA-N 2-[6-(methoxymethyl)-2-[3-methoxy-4-(4-methylimidazol-1-yl)anilino]pyrimidin-4-yl]propan-2-ol Chemical compound COCC1=CC(C(C)(C)O)=NC(NC=2C=C(OC)C(=CC=2)N2C=C(C)N=C2)=N1 IOBDVBVNPMCPMC-UHFFFAOYSA-N 0.000 claims description 4
229960004372 aripiprazole Drugs 0.000 claims description 4
229960004170 clozapine Drugs 0.000 claims description 4
208000010877 cognitive disease Diseases 0.000 claims description 4
229960002464 fluoxetine Drugs 0.000 claims description 4
229960003980 galantamine Drugs 0.000 claims description 4
ASUTZQLVASHGKV-UHFFFAOYSA-N galanthamine hydrochloride Natural products O1C(=C23)C(OC)=CC=C2CN(C)CCC23C1CC(O)C=C2 ASUTZQLVASHGKV-UHFFFAOYSA-N 0.000 claims description 4
YAAWASYJIRZXSZ-UHFFFAOYSA-N pyrimidine-2,4-diamine Chemical compound NC1=CC=NC(N)=N1 YAAWASYJIRZXSZ-UHFFFAOYSA-N 0.000 claims description 4
229960001534 risperidone Drugs 0.000 claims description 4
229960004136 rivastigmine Drugs 0.000 claims description 4
229960000607 ziprasidone Drugs 0.000 claims description 4
YJQWOLFZVCPXGK-UHFFFAOYSA-N 1-[2-[3-methoxy-4-(4-methoxyimidazol-1-yl)anilino]-6-(2,2,2-trifluoroethoxymethyl)pyrimidin-4-yl]ethanol Chemical compound C1=NC(OC)=CN1C(C(=C1)OC)=CC=C1NC1=NC(COCC(F)(F)F)=CC(C(C)O)=N1 YJQWOLFZVCPXGK-UHFFFAOYSA-N 0.000 claims description 3
XAOCKFGTPHMXGH-UHFFFAOYSA-N 1-[2-[3-methoxy-4-(4-methylimidazol-1-yl)anilino]-6-(2,2,2-trifluoroethoxymethyl)pyrimidin-4-yl]-2-methylpropan-1-ol Chemical compound C=1C=C(N2C=C(C)N=C2)C(OC)=CC=1NC1=NC(COCC(F)(F)F)=CC(C(O)C(C)C)=N1 XAOCKFGTPHMXGH-UHFFFAOYSA-N 0.000 claims description 3
BUBAHBRWIZRTJR-UHFFFAOYSA-N 1-[2-[3-methoxy-4-(4-methylimidazol-1-yl)anilino]-6-(2,2,2-trifluoroethoxymethyl)pyrimidin-4-yl]ethanol Chemical compound C=1C=C(N2C=C(C)N=C2)C(OC)=CC=1NC1=NC(COCC(F)(F)F)=CC(C(C)O)=N1 BUBAHBRWIZRTJR-UHFFFAOYSA-N 0.000 claims description 3
CDUINTDPTHLEDE-UHFFFAOYSA-N 1-[[2-[3-methoxy-4-(4-methylimidazol-1-yl)anilino]-6-(2,2,2-trifluoroethoxymethyl)pyrimidin-4-yl]amino]-2-methylpropan-2-ol Chemical compound C=1C=C(N2C=C(C)N=C2)C(OC)=CC=1NC1=NC(COCC(F)(F)F)=CC(NCC(C)(C)O)=N1 CDUINTDPTHLEDE-UHFFFAOYSA-N 0.000 claims description 3
OQPFNFZAOVYKTL-UHFFFAOYSA-N 2-[2-[3-methoxy-4-(4-methylimidazol-1-yl)anilino]-6-(2,2,2-trifluoroethoxymethyl)pyrimidin-4-yl]butan-2-ol Chemical compound CCC(C)(O)C1=CC(COCC(F)(F)F)=NC(NC=2C=C(OC)C(=CC=2)N2C=C(C)N=C2)=N1 OQPFNFZAOVYKTL-UHFFFAOYSA-N 0.000 claims description 3
HWFMQHNCLUXIHR-UHFFFAOYSA-N 2-[2-[3-methoxy-4-(4-methylimidazol-1-yl)anilino]-6-(2,2,2-trifluoroethoxymethyl)pyrimidin-4-yl]propan-2-ol Chemical compound C=1C=C(N2C=C(C)N=C2)C(OC)=CC=1NC1=NC(COCC(F)(F)F)=CC(C(C)(C)O)=N1 HWFMQHNCLUXIHR-UHFFFAOYSA-N 0.000 claims description 3
FGEODWQZAMQRTK-UHFFFAOYSA-N 2-[2-[3-methoxy-4-(4-methylimidazol-1-yl)anilino]-6-(3,3,3-trifluoropropoxymethyl)pyrimidin-4-yl]propan-2-ol Chemical compound C=1C=C(N2C=C(C)N=C2)C(OC)=CC=1NC1=NC(COCCC(F)(F)F)=CC(C(C)(C)O)=N1 FGEODWQZAMQRTK-UHFFFAOYSA-N 0.000 claims description 3
KNWHEQXEAMCNQN-UHFFFAOYSA-N 2-[6-(cyclopropylmethoxymethyl)-2-[3-methoxy-4-(4-methylimidazol-1-yl)anilino]pyrimidin-4-yl]propan-2-ol Chemical compound C=1C=C(N2C=C(C)N=C2)C(OC)=CC=1NC(N=C(C=1)C(C)(C)O)=NC=1COCC1CC1 KNWHEQXEAMCNQN-UHFFFAOYSA-N 0.000 claims description 3
CUYWDQUWJUSFRW-UHFFFAOYSA-N 2-cyclopropyl-1-[2-[3-methoxy-4-(4-methylimidazol-1-yl)anilino]-6-(2,2,2-trifluoroethoxymethyl)pyrimidin-4-yl]ethanol Chemical compound C=1C=C(N2C=C(C)N=C2)C(OC)=CC=1NC(N=1)=NC(COCC(F)(F)F)=CC=1C(O)CC1CC1 CUYWDQUWJUSFRW-UHFFFAOYSA-N 0.000 claims description 3
ZNSHPICMEBTIDG-UHFFFAOYSA-N 3-[[2-[3-methoxy-4-(4-methylimidazol-1-yl)anilino]-6-(2,2,2-trifluoroethoxymethyl)pyrimidin-4-yl]amino]propanenitrile Chemical compound C=1C=C(N2C=C(C)N=C2)C(OC)=CC=1NC1=NC(COCC(F)(F)F)=CC(NCCC#N)=N1 ZNSHPICMEBTIDG-UHFFFAOYSA-N 0.000 claims description 3
WETTXVVWUDYFEV-UHFFFAOYSA-N 4-(azetidin-1-yl)-n-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]-6-(2,2,2-trifluoroethoxymethyl)pyrimidin-2-amine Chemical compound C=1C=C(N2C=C(C)N=C2)C(OC)=CC=1NC(N=1)=NC(COCC(F)(F)F)=CC=1N1CCC1 WETTXVVWUDYFEV-UHFFFAOYSA-N 0.000 claims description 3
MYGVFZNIOCVSMR-UHFFFAOYSA-N 4-[(3-fluoroazetidin-1-yl)methyl]-n-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]-6-(2,2,2-trifluoroethoxymethyl)pyrimidin-2-amine Chemical compound C=1C=C(N2C=C(C)N=C2)C(OC)=CC=1NC(N=1)=NC(COCC(F)(F)F)=CC=1CN1CC(F)C1 MYGVFZNIOCVSMR-UHFFFAOYSA-N 0.000 claims description 3
HEYWBCWIRSVHLW-UHFFFAOYSA-N 4-[(dimethylamino)methyl]-n-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]-6-(2,2,2-trifluoroethoxymethyl)pyrimidin-2-amine Chemical compound C=1C=C(N2C=C(C)N=C2)C(OC)=CC=1NC1=NC(COCC(F)(F)F)=CC(CN(C)C)=N1 HEYWBCWIRSVHLW-UHFFFAOYSA-N 0.000 claims description 3
NXIJKQAXXRFXRS-UHFFFAOYSA-N 4-n-(2-methoxyethyl)-2-n-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]-6-(2,2,2-trifluoroethoxymethyl)pyrimidine-2,4-diamine Chemical compound COCCNC1=CC(COCC(F)(F)F)=NC(NC=2C=C(OC)C(=CC=2)N2C=C(C)N=C2)=N1 NXIJKQAXXRFXRS-UHFFFAOYSA-N 0.000 claims description 3
MXANQQONSNDYOB-UHFFFAOYSA-N 4-n-benzyl-2-n-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]-4-n-methyl-6-(2,2,2-trifluoroethoxymethyl)pyrimidine-2,4-diamine Chemical compound C=1C=C(N2C=C(C)N=C2)C(OC)=CC=1NC(N=1)=NC(COCC(F)(F)F)=CC=1N(C)CC1=CC=CC=C1 MXANQQONSNDYOB-UHFFFAOYSA-N 0.000 claims description 3
NWAZCFKNPYIPFM-UHFFFAOYSA-N 4-n-cyclopropyl-2-n-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]-6-(2,2,2-trifluoroethoxymethyl)pyrimidine-2,4-diamine Chemical compound C=1C=C(N2C=C(C)N=C2)C(OC)=CC=1NC(N=1)=NC(COCC(F)(F)F)=CC=1NC1CC1 NWAZCFKNPYIPFM-UHFFFAOYSA-N 0.000 claims description 3
OOFOLNCXBGEMHJ-UHFFFAOYSA-N 6-(cyclopropylmethoxymethyl)-2-n-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]-4-n-methylpyrimidine-2,4-diamine Chemical compound N=1C(NC=2C=C(OC)C(=CC=2)N2C=C(C)N=C2)=NC(NC)=CC=1COCC1CC1 OOFOLNCXBGEMHJ-UHFFFAOYSA-N 0.000 claims description 3
208000000044 Amnesia Diseases 0.000 claims description 3
108010090849 Amyloid beta-Peptides Proteins 0.000 claims description 3
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229940121363 anti-inflammatory agent Drugs 0.000 claims description 3
239000002260 anti-inflammatory agent Substances 0.000 claims description 3
239000000544 cholinesterase inhibitor Substances 0.000 claims description 3
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
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125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 2
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230000001225 therapeutic effect Effects 0.000 description 1
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BUGOPWGPQGYYGR-UHFFFAOYSA-N thiane 1,1-dioxide Chemical compound O=S1(=O)CCCCC1 BUGOPWGPQGYYGR-UHFFFAOYSA-N 0.000 description 1
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HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 description 1
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ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
ZEWQUBUPAILYHI-UHFFFAOYSA-N trifluoperazine Chemical compound C1CN(C)CCN1CCCN1C2=CC(C(F)(F)F)=CC=C2SC2=CC=CC=C21 ZEWQUBUPAILYHI-UHFFFAOYSA-N 0.000 description 1
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ZSCDBOWYZJWBIY-UHFFFAOYSA-N trimipramine Chemical compound C1CC2=CC=CC=C2N(CC(CN(C)C)C)C2=CC=CC=C21 ZSCDBOWYZJWBIY-UHFFFAOYSA-N 0.000 description 1
229910052722 tritium Inorganic materials 0.000 description 1
DTMPGSXFUXZBDK-UHFFFAOYSA-N uldazepam Chemical compound C12=CC(Cl)=CC=C2N=C(NOCC=C)CN=C1C1=CC=CC=C1Cl DTMPGSXFUXZBDK-UHFFFAOYSA-N 0.000 description 1
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LNPDTQAFDNKSHK-UHFFFAOYSA-N valdecoxib Chemical compound CC=1ON=C(C=2C=CC=CC=2)C=1C1=CC=C(S(N)(=O)=O)C=C1 LNPDTQAFDNKSHK-UHFFFAOYSA-N 0.000 description 1
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HUNXMJYCHXQEGX-UHFFFAOYSA-N zaleplon Chemical compound CCN(C(C)=O)C1=CC=CC(C=2N3N=CC(=C3N=CC=2)C#N)=C1 HUNXMJYCHXQEGX-UHFFFAOYSA-N 0.000 description 1
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UTAZCRNOSWWEFR-ZDUSSCGKSA-N zolmitriptan Chemical compound C=1[C]2C(CCN(C)C)=CN=C2C=CC=1C[C@H]1COC(=O)N1 UTAZCRNOSWWEFR-ZDUSSCGKSA-N 0.000 description 1
ZAFYATHCZYHLPB-UHFFFAOYSA-N zolpidem Chemical compound N1=C2C=CC(C)=CN2C(CC(=O)N(C)C)=C1C1=CC=C(C)C=C1 ZAFYATHCZYHLPB-UHFFFAOYSA-N 0.000 description 1
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229960000820 zopiclone Drugs 0.000 description 1
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HDOZVRUNCMBHFH-UHFFFAOYSA-N zotepine Chemical compound CN(C)CCOC1=CC2=CC=CC=C2SC2=CC=C(Cl)C=C12 HDOZVRUNCMBHFH-UHFFFAOYSA-N 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Epidemiology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Psychology (AREA)
Psychiatry (AREA)
Hospice & Palliative Care (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

DK14727562.2T 2013-06-04 2014-06-03 PYRIMIDE COMPOUNDS AND THEIR USE AS GAMMA SECRETASE MODULATORS DK3004079T3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
SE1350685		2013-06-04
PCT/EP2014/061503 WO2014195323A1 (en)	2013-06-04	2014-06-03	Pyrimidine compounds and their use as gamma secretase modulators

Publications (1)

Publication Number	Publication Date
DK3004079T3 true DK3004079T3 (en)	2018-04-16

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DK14727562.2T DK3004079T3 (en)	2013-06-04	2014-06-03	PYRIMIDE COMPOUNDS AND THEIR USE AS GAMMA SECRETASE MODULATORS

Country Status (9)

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US (1)	US9439904B2 (2)
EP (1)	EP3004079B1 (2)
JP (1)	JP6368777B2 (2)
CN (1)	CN105263923B (2)
DK (1)	DK3004079T3 (2)
ES (1)	ES2665421T3 (2)
NO (1)	NO3004079T3 (2)
PL (1)	PL3004079T3 (2)
WO (1)	WO2014195323A1 (2)

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Publication number	Publication date
CN105263923A (zh)	2016-01-20
ES2665421T3 (es)	2018-04-25
JP6368777B2 (ja)	2018-08-01
WO2014195323A1 (en)	2014-12-11
EP3004079A1 (en)	2016-04-13
PL3004079T3 (pl)	2018-07-31
CN105263923B (zh)	2017-06-23
EP3004079B1 (en)	2018-01-17
NO3004079T3 (2)	2018-06-16
US20160129002A1 (en)	2016-05-12
US9439904B2 (en)	2016-09-13
JP2016520637A (ja)	2016-07-14

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WO2015067770A1 (en)	2015-05-14	Triazolopyrazine derivatives as brd4 inhibitors
EP2978757A1 (en)	2016-02-03	Indolinone analogues as brd4 inhibitors
EA009620B1 (ru)	2008-02-28	Производные 2,3,6-тризамещённого-4-пиримидона
WO2011088027A1 (en)	2011-07-21	Compounds and methods
EP3287454B1 (en)	2020-09-02	Heterocyclic compound
TW201040169A (en)	2010-11-16	Imidazole substituted pyrimidines 724
US20120122843A1 (en)	2012-05-17	Compounds and Their Use for Treatment of Amyloid Beta-Related Diseases
US9611254B2 (en)	2017-04-04	Triazole compounds and their use as gamma secretase modulators
WO2015066697A1 (en)	2015-05-07	Fused morpholinopyrimidines and methods of use thereof
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CN107207516A (zh)	2017-09-26	八氢吡咯并[3,4‑c]吡咯衍生物及其用途