ZA200601101B - Cyclic amine BACE-1 inhibitors having a heterocyclic substituent - Google Patents

Cyclic amine BACE-1 inhibitors having a heterocyclic substituent Download PDF

Info

Publication number: ZA200601101B
Authority: ZA; South Africa
Prior art keywords: alkyl; heteroaryl; compound; cycloalkylalkyl; cycloalkyl
Prior art date: 2003-08-08

Application number

ZA200601101A

Other languages

English (en)

Inventor

Jared N Cumming

Li Gouqing

Stamford Andrew

Johannes H Voigt

Pan Jianping

Douglas W Hobbs

Jeffrey F Lowrie

Huang Ying

Iserloh Ulrich

Strickland Corey

Wu Yusheng

Guo Tao

Thuy X H Le

Original Assignee

Schering Corp

Pharmacopeia Drug Discovery

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.)

2003-08-08

Filing date

2006-02-07

Publication date

2007-05-30

2006-02-07 Application filed by Schering Corp, Pharmacopeia Drug Discovery filed Critical Schering Corp

2007-05-30 Publication of ZA200601101B publication Critical patent/ZA200601101B/en

Links

-1 Cyclic amine Chemical class 0.000 title claims description 102
229940125759 BACE1 protease inhibitor Drugs 0.000 title description 4
125000000217 alkyl group Chemical group 0.000 claims description 113
150000001875 compounds Chemical class 0.000 claims description 85
125000001072 heteroaryl group Chemical group 0.000 claims description 68
125000003118 aryl group Chemical group 0.000 claims description 52
229910052739 hydrogen Inorganic materials 0.000 claims description 51
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 50
125000000753 cycloalkyl group Chemical group 0.000 claims description 48
125000003710 aryl alkyl group Chemical group 0.000 claims description 47
125000003342 alkenyl group Chemical group 0.000 claims description 38
239000001257 hydrogen Substances 0.000 claims description 38
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 37
125000004446 heteroarylalkyl group Chemical group 0.000 claims description 35
125000000304 alkynyl group Chemical group 0.000 claims description 33
125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 27
150000003839 salts Chemical class 0.000 claims description 25
125000001424 substituent group Chemical group 0.000 claims description 25
125000003545 alkoxy group Chemical group 0.000 claims description 23
238000000034 method Methods 0.000 claims description 23
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
229910052799 carbon Inorganic materials 0.000 claims description 21
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 19
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
239000000203 mixture Substances 0.000 claims description 17
125000004093 cyano group Chemical group *C#N 0.000 claims description 16
208000024827 Alzheimer disease Diseases 0.000 claims description 14
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 14
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
239000012453 solvate Substances 0.000 claims description 13
239000000126 substance Substances 0.000 claims description 13
238000011282 treatment Methods 0.000 claims description 12
230000001149 cognitive effect Effects 0.000 claims description 10
125000001188 haloalkyl group Chemical group 0.000 claims description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
229910052757 nitrogen Inorganic materials 0.000 claims description 10
229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims description 9
239000000544 cholinesterase inhibitor Substances 0.000 claims description 9
208000010877 cognitive disease Diseases 0.000 claims description 9
239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
230000004770 neurodegeneration Effects 0.000 claims description 9
208000015122 neurodegenerative disease Diseases 0.000 claims description 9
229940121773 Secretase inhibitor Drugs 0.000 claims description 8
230000015572 biosynthetic process Effects 0.000 claims description 8
239000003112 inhibitor Substances 0.000 claims description 8
125000004076 pyridyl group Chemical group 0.000 claims description 7
229940122041 Cholinesterase inhibitor Drugs 0.000 claims description 6
239000003540 gamma secretase inhibitor Substances 0.000 claims description 6
230000002401 inhibitory effect Effects 0.000 claims description 6
125000001544 thienyl group Chemical group 0.000 claims description 6
239000003795 chemical substances by application Substances 0.000 claims description 5
230000008021 deposition Effects 0.000 claims description 5
239000003814 drug Substances 0.000 claims description 5
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
239000008194 pharmaceutical composition Substances 0.000 claims description 5
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 5
125000003226 pyrazolyl group Chemical group 0.000 claims description 5
230000003637 steroidlike Effects 0.000 claims description 5
229910052717 sulfur Inorganic materials 0.000 claims description 5
RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
125000003373 pyrazinyl group Chemical group 0.000 claims description 4
125000000335 thiazolyl group Chemical group 0.000 claims description 4
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
102000004868 N-Methyl-D-Aspartate Receptors Human genes 0.000 claims description 3
108090001041 N-Methyl-D-Aspartate Receptors Proteins 0.000 claims description 3
229940099433 NMDA receptor antagonist Drugs 0.000 claims description 3
125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 3
125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
239000003703 n methyl dextro aspartic acid receptor blocking agent Substances 0.000 claims description 3
230000000926 neurological effect Effects 0.000 claims description 3
239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims description 3
229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims description 3
125000002971 oxazolyl group Chemical group 0.000 claims description 3
125000003884 phenylalkyl group Chemical group 0.000 claims description 3
125000000547 substituted alkyl group Chemical group 0.000 claims description 3
208000037259 Amyloid Plaque Diseases 0.000 claims description 2
125000004423 acyloxy group Chemical group 0.000 claims description 2
125000004103 aminoalkyl group Chemical group 0.000 claims description 2
230000003110 anti-inflammatory effect Effects 0.000 claims description 2
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
150000001721 carbon Chemical group 0.000 claims description 2
125000004984 dialkylaminoalkoxy group Chemical group 0.000 claims description 2
125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 2
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 11
125000001475 halogen functional group Chemical group 0.000 claims 10
150000002431 hydrogen Chemical class 0.000 claims 6
229940125373 Gamma-Secretase Inhibitor Drugs 0.000 claims 3
229940044551 receptor antagonist Drugs 0.000 claims 3
239000002464 receptor antagonist Substances 0.000 claims 3
102000002659 Amyloid Precursor Protein Secretases Human genes 0.000 claims 2
108010043324 Amyloid Precursor Protein Secretases Proteins 0.000 claims 2
102000003914 Cholinesterases Human genes 0.000 claims 2
108090000322 Cholinesterases Proteins 0.000 claims 2
229940048961 cholinesterase Drugs 0.000 claims 2
230000000626 neurodegenerative effect Effects 0.000 claims 2
HOKKHZGPKSLGJE-GSVOUGTGSA-N N-Methyl-D-aspartic acid Chemical compound CN[C@@H](C(O)=O)CC(O)=O HOKKHZGPKSLGJE-GSVOUGTGSA-N 0.000 claims 1
229940123934 Reductase inhibitor Drugs 0.000 claims 1
229920000180 alkyd Polymers 0.000 claims 1
239000005557 antagonist Substances 0.000 claims 1
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
229960004717 insulin aspart Drugs 0.000 claims 1
239000003595 mist Substances 0.000 claims 1
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
ICSAXRANXQSPQP-VUKDEKJYSA-M sodium;(5r,6s)-6-[(1r)-1-hydroxyethyl]-7-oxo-3-[(2r)-oxolan-2-yl]-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate Chemical compound [Na+].S([C@@H]1[C@H](C(N1C=1C([O-])=O)=O)[C@H](O)C)C=1[C@H]1CCCO1 ICSAXRANXQSPQP-VUKDEKJYSA-M 0.000 claims 1
239000002294 steroidal antiinflammatory agent Substances 0.000 claims 1
125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 claims 1
235000013350 formula milk Nutrition 0.000 description 41
125000004432 carbon atom Chemical group C* 0.000 description 15
125000005843 halogen group Chemical group 0.000 description 12
125000004122 cyclic group Chemical group 0.000 description 10
125000006413 ring segment Chemical group 0.000 description 9
101710137189 Amyloid-beta A4 protein Proteins 0.000 description 8
101710151993 Amyloid-beta precursor protein Proteins 0.000 description 8
102100022704 Amyloid-beta precursor protein Human genes 0.000 description 8
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 8
DZHSAHHDTRWUTF-SIQRNXPUSA-N amyloid-beta polypeptide 42 Chemical compound C([C@@H](C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@H](C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)NCC(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(O)=O)[C@@H](C)CC)C(C)C)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@@H](NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)CNC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC(O)=O)C(C)C)C(C)C)C1=CC=CC=C1 DZHSAHHDTRWUTF-SIQRNXPUSA-N 0.000 description 8
125000000623 heterocyclic group Chemical group 0.000 description 8
229940002612 prodrug Drugs 0.000 description 8
239000000651 prodrug Substances 0.000 description 8
125000004429 atom Chemical group 0.000 description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
229910052760 oxygen Inorganic materials 0.000 description 6
239000001301 oxygen Substances 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 5
239000002253 acid Substances 0.000 description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
125000006242 amine protecting group Chemical group 0.000 description 4
239000002585 base Substances 0.000 description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
230000000694 effects Effects 0.000 description 4
125000005842 heteroatom Chemical group 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
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SORGEQQSQGNZFI-UHFFFAOYSA-N [azido(phenoxy)phosphoryl]oxybenzene Chemical compound C=1C=CC=CC=1OP(=O)(N=[N+]=[N-])OC1=CC=CC=C1 SORGEQQSQGNZFI-UHFFFAOYSA-N 0.000 description 3
125000002252 acyl group Chemical group 0.000 description 3
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150000001412 amines Chemical class 0.000 description 3
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FPIRBHDGWMWJEP-UHFFFAOYSA-N 1-hydroxy-7-azabenzotriazole Chemical compound C1=CN=C2N(O)N=NC2=C1 FPIRBHDGWMWJEP-UHFFFAOYSA-N 0.000 description 2
IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 2
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150000003254 radicals Chemical class 0.000 description 1
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229960000672 rosuvastatin Drugs 0.000 description 1
BPRHUIZQVSMCRT-VEUZHWNKSA-N rosuvastatin Chemical compound CC(C)C1=NC(N(C)S(C)(=O)=O)=NC(C=2C=CC(F)=CC=2)=C1\C=C\[C@@H](O)C[C@@H](O)CC(O)=O BPRHUIZQVSMCRT-VEUZHWNKSA-N 0.000 description 1
150000003873 salicylate salts Chemical class 0.000 description 1
239000004576 sand Substances 0.000 description 1
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239000007787 solid Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
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238000003786 synthesis reaction Methods 0.000 description 1
229960001685 tacrine Drugs 0.000 description 1
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YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
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125000003507 tetrahydrothiofenyl group Chemical group 0.000 description 1
125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 description 1
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229960001017 tolmetin Drugs 0.000 description 1
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LBLYYCQCTBFVLH-UHFFFAOYSA-M toluenesulfonate group Chemical group C=1(C(=CC=CC1)S(=O)(=O)[O-])C LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
125000005490 tosylate group Chemical group 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical class CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
150000003751 zinc Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B35/00—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
- C04B35/622—Forming processes; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
- C04B35/626—Preparing or treating the powders individually or as batches ; preparing or treating macroscopic reinforcing agents for ceramic products, e.g. fibres; mechanical aspects section B
- C04B35/63—Preparing or treating the powders individually or as batches ; preparing or treating macroscopic reinforcing agents for ceramic products, e.g. fibres; mechanical aspects section B using additives specially adapted for forming the products, e.g.. binder binders
- C04B35/632—Organic additives
- 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
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/273—2-Pyrrolidones with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
- C07D207/277—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
- 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
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- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
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- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Health & Medical Sciences (AREA)
Ceramic Engineering (AREA)
Manufacturing & Machinery (AREA)
Animal Behavior & Ethology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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Inorganic Chemistry (AREA)
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Hospice & Palliative Care (AREA)
Psychiatry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Pyrrole Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

ZA200601101A 2003-08-08 2006-02-07 Cyclic amine BACE-1 inhibitors having a heterocyclic substituent ZA200601101B (en)

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US49364603P	2003-08-08	2003-08-08

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ZA200601101B true ZA200601101B (en)	2007-05-30

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ZA200601101A ZA200601101B (en)	2003-08-08	2006-02-07	Cyclic amine BACE-1 inhibitors having a heterocyclic substituent

Country Status (17)

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US (2)	US7598250B2 (de)
EP (1)	EP1660447B1 (de)
JP (2)	JP4472700B2 (de)
KR (1)	KR20060056376A (de)
CN (1)	CN1863770B (de)
AR (1)	AR045219A1 (de)
AT (1)	ATE402921T1 (de)
AU (1)	AU2004263532A1 (de)
CA (1)	CA2534672A1 (de)
DE (1)	DE602004015476D1 (de)
ES (1)	ES2308247T3 (de)
IL (1)	IL173534A0 (de)
MX (1)	MXPA06001558A (de)
PE (1)	PE20050354A1 (de)
TW (1)	TW200524910A (de)
WO (1)	WO2005014540A1 (de)
ZA (1)	ZA200601101B (de)

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2004
- 2004-08-04 MX MXPA06001558A patent/MXPA06001558A/es active IP Right Grant
- 2004-08-04 JP JP2006522800A patent/JP4472700B2/ja not_active Expired - Fee Related
- 2004-08-04 EP EP04780561A patent/EP1660447B1/de not_active Expired - Lifetime
- 2004-08-04 CN CN2004800290969A patent/CN1863770B/zh not_active Expired - Fee Related
- 2004-08-04 AT AT04780561T patent/ATE402921T1/de not_active IP Right Cessation
- 2004-08-04 AU AU2004263532A patent/AU2004263532A1/en not_active Abandoned
- 2004-08-04 ES ES04780561T patent/ES2308247T3/es not_active Expired - Lifetime
- 2004-08-04 DE DE602004015476T patent/DE602004015476D1/de not_active Expired - Lifetime
- 2004-08-04 CA CA002534672A patent/CA2534672A1/en not_active Abandoned
- 2004-08-04 AR ARP040102781A patent/AR045219A1/es unknown
- 2004-08-04 TW TW093123376A patent/TW200524910A/zh unknown
- 2004-08-04 KR KR1020067002698A patent/KR20060056376A/ko not_active Ceased
- 2004-08-04 WO PCT/US2004/025748 patent/WO2005014540A1/en not_active Ceased
- 2004-08-04 US US10/911,030 patent/US7598250B2/en not_active Expired - Lifetime
- 2004-08-05 PE PE2004000758A patent/PE20050354A1/es not_active Application Discontinuation
2006
- 2006-02-05 IL IL173534A patent/IL173534A0/en unknown
- 2006-02-07 ZA ZA200601101A patent/ZA200601101B/en unknown
2009
- 2009-06-24 US US12/490,884 patent/US7910590B2/en not_active Expired - Lifetime
- 2009-11-27 JP JP2009270850A patent/JP2010047610A/ja not_active Withdrawn

Also Published As

Publication number	Publication date
JP2010047610A (ja)	2010-03-04
ES2308247T3 (es)	2008-12-01
EP1660447B1 (de)	2008-07-30
JP2007501803A (ja)	2007-02-01
EP1660447A1 (de)	2006-05-31
WO2005014540A1 (en)	2005-02-17
AU2004263532A1 (en)	2005-02-17
AR045219A1 (es)	2005-10-19
JP4472700B2 (ja)	2010-06-02
US7598250B2 (en)	2009-10-06
US7910590B2 (en)	2011-03-22
US20050043290A1 (en)	2005-02-24
CN1863770B (zh)	2011-05-25
US20090312341A1 (en)	2009-12-17
CA2534672A1 (en)	2005-02-17
ATE402921T1 (de)	2008-08-15
IL173534A0 (en)	2006-07-05
DE602004015476D1 (de)	2008-09-11
CN1863770A (zh)	2006-11-15
PE20050354A1 (es)	2005-05-17
KR20060056376A (ko)	2006-05-24
MXPA06001558A (es)	2006-05-15
TW200524910A (en)	2005-08-01

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