ZA200303411B - Lactam compound. - Google Patents
Lactam compound. Download PDFInfo
- Publication number
- ZA200303411B ZA200303411B ZA200303411A ZA200303411A ZA200303411B ZA 200303411 B ZA200303411 B ZA 200303411B ZA 200303411 A ZA200303411 A ZA 200303411A ZA 200303411 A ZA200303411 A ZA 200303411A ZA 200303411 B ZA200303411 B ZA 200303411B
- Authority
- ZA
- South Africa
- Prior art keywords
- methyl
- formula
- amino
- compound
- hydroxy
- Prior art date
Links
- -1 Lactam compound Chemical class 0.000 title claims description 30
- 238000000034 method Methods 0.000 claims description 78
- 150000001875 compounds Chemical class 0.000 claims description 69
- 125000000217 alkyl group Chemical group 0.000 claims description 43
- 125000003118 aryl group Chemical group 0.000 claims description 43
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 34
- 125000001072 heteroaryl group Chemical group 0.000 claims description 33
- 239000000126 substance Substances 0.000 claims description 32
- 239000000203 mixture Substances 0.000 claims description 31
- 125000000623 heterocyclic group Chemical group 0.000 claims description 29
- 150000004683 dihydrates Chemical class 0.000 claims description 22
- 208000024827 Alzheimer disease Diseases 0.000 claims description 20
- 125000003342 alkenyl group Chemical group 0.000 claims description 19
- 150000003951 lactams Chemical class 0.000 claims description 19
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 19
- 125000000304 alkynyl group Chemical group 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 15
- 230000008878 coupling Effects 0.000 claims description 14
- 238000010168 coupling process Methods 0.000 claims description 14
- 238000005859 coupling reaction Methods 0.000 claims description 14
- 230000002401 inhibitory effect Effects 0.000 claims description 14
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 14
- 125000002252 acyl group Chemical group 0.000 claims description 13
- 125000004423 acyloxy group Chemical group 0.000 claims description 13
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 13
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 13
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 13
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 13
- 125000000266 alpha-aminoacyl group Chemical group 0.000 claims description 12
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims description 10
- 230000015572 biosynthetic process Effects 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 10
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 10
- 238000003786 synthesis reaction Methods 0.000 claims description 10
- 230000003213 activating effect Effects 0.000 claims description 9
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 9
- 238000002425 crystallisation Methods 0.000 claims description 9
- 230000008025 crystallization Effects 0.000 claims description 9
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 9
- 125000004104 aryloxy group Chemical group 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 8
- MIOPJNTWMNEORI-XVKPBYJWSA-N (R)-camphorsulfonic acid Chemical compound C1C[C@]2(CS(O)(=O)=O)C(=O)C[C@H]1C2(C)C MIOPJNTWMNEORI-XVKPBYJWSA-N 0.000 claims description 7
- 239000007787 solid Substances 0.000 claims description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- 239000003125 aqueous solvent Substances 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 208000031124 Dementia Alzheimer type Diseases 0.000 claims description 5
- 238000005481 NMR spectroscopy Methods 0.000 claims description 4
- 125000006242 amine protecting group Chemical group 0.000 claims description 3
- 238000010511 deprotection reaction Methods 0.000 claims description 3
- 238000001640 fractional crystallisation Methods 0.000 claims description 3
- 125000004043 oxo group Chemical group O=* 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 22
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 claims 11
- 125000003412 L-alanyl group Chemical group [H]N([H])[C@@](C([H])([H])[H])(C(=O)[*])[H] 0.000 claims 10
- NSFIAKFOCAEBER-ROUUACIJSA-N (2r,3r)-2,3-dihydroxy-2,3-bis(4-methylphenyl)butanedioic acid Chemical compound C1=CC(C)=CC=C1[C@](O)(C(O)=O)[C@@](O)(C(O)=O)C1=CC=C(C)C=C1 NSFIAKFOCAEBER-ROUUACIJSA-N 0.000 claims 9
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 8
- 238000002360 preparation method Methods 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 7
- AYQMNFRCBKOMIA-UHFFFAOYSA-N 1-benzazepin-2-one Chemical compound O=C1C=CC=C2C=CC=CC2=N1 AYQMNFRCBKOMIA-UHFFFAOYSA-N 0.000 claims 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 4
- 150000001299 aldehydes Chemical class 0.000 claims 4
- 230000002265 prevention Effects 0.000 claims 3
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 claims 2
- IHFRMUGEILMHNU-UHFFFAOYSA-N 2-hydroxy-5-nitrobenzaldehyde Chemical compound OC1=CC=C([N+]([O-])=O)C=C1C=O IHFRMUGEILMHNU-UHFFFAOYSA-N 0.000 claims 2
- FABVMBDCVAJXMB-UHFFFAOYSA-N 3,5-dichloro-2-hydroxybenzaldehyde Chemical compound OC1=C(Cl)C=C(Cl)C=C1C=O FABVMBDCVAJXMB-UHFFFAOYSA-N 0.000 claims 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims 2
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims 2
- 229940024606 amino acid Drugs 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 150000002923 oximes Chemical class 0.000 claims 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 claims 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims 2
- NGEWQZIDQIYUNV-BYPYZUCNSA-N (S)-2-hydroxy-3-methylbutyric acid Chemical compound CC(C)[C@H](O)C(O)=O NGEWQZIDQIYUNV-BYPYZUCNSA-N 0.000 claims 1
- GYIYVTGAOWHWRI-UHFFFAOYSA-N 1,2,3,5-tetrahydro-3-benzazepin-4-one Chemical compound C1CNC(=O)CC2=CC=CC=C21 GYIYVTGAOWHWRI-UHFFFAOYSA-N 0.000 claims 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 claims 1
- 229960002510 mandelic acid Drugs 0.000 claims 1
- 230000002250 progressing effect Effects 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 description 18
- 125000001424 substituent group Chemical group 0.000 description 17
- 125000002947 alkylene group Chemical group 0.000 description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
- 239000000523 sample Substances 0.000 description 10
- 238000000227 grinding Methods 0.000 description 8
- 125000004442 acylamino group Chemical group 0.000 description 7
- 229930194542 Keto Natural products 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 125000000468 ketone group Chemical group 0.000 description 6
- 125000005323 thioketone group Chemical group 0.000 description 6
- 229910052736 halogen Inorganic materials 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- 150000003573 thiols Chemical class 0.000 description 5
- 125000004450 alkenylene group Chemical group 0.000 description 4
- 238000000371 solid-state nuclear magnetic resonance spectroscopy Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000004570 mortar (masonry) Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000005384 cross polarization magic-angle spinning Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- YUWFEBAXEOLKSG-UHFFFAOYSA-N hexamethylbenzene Chemical compound CC1=C(C)C(C)=C(C)C(C)=C1C YUWFEBAXEOLKSG-UHFFFAOYSA-N 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 238000010996 solid-state NMR spectroscopy Methods 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- OCQAXYHNMWVLRH-UHFFFAOYSA-N 2,3-dibenzoyl-2,3-dihydroxybutanedioic acid Chemical compound C=1C=CC=CC=1C(=O)C(O)(C(O)=O)C(O)(C(=O)O)C(=O)C1=CC=CC=C1 OCQAXYHNMWVLRH-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- LCRVSUZIDWQHIN-UHFFFAOYSA-N 3-methyl-2,5,8,9-tetrahydro-1h-3-benzazepin-4-one Chemical compound C1C(=O)N(C)CCC2=C1C=CCC2 LCRVSUZIDWQHIN-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- MNQZXJOMYWMBOU-VKHMYHEASA-N D-glyceraldehyde Chemical class OC[C@@H](O)C=O MNQZXJOMYWMBOU-VKHMYHEASA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 238000005004 MAS NMR spectroscopy Methods 0.000 description 1
- OGPWFDIMIQRSNZ-UHFFFAOYSA-N O.O.C1C(NCCC2=C1C=CC=C2)=O Chemical compound O.O.C1C(NCCC2=C1C=CC=C2)=O OGPWFDIMIQRSNZ-UHFFFAOYSA-N 0.000 description 1
- QNDJAWHAWZGWHH-UHFFFAOYSA-N O.O.CC1C(NCCC2=C1C=CCC2)=O Chemical compound O.O.CC1C(NCCC2=C1C=CCC2)=O QNDJAWHAWZGWHH-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- ZVLDJSZFKQJMKD-UHFFFAOYSA-N [Li].[Si] Chemical compound [Li].[Si] ZVLDJSZFKQJMKD-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000000033 alkoxyamino group Chemical group 0.000 description 1
- 125000005055 alkyl alkoxy group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005251 capillar electrophoresis Methods 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 238000004296 chiral HPLC Methods 0.000 description 1
- 238000005388 cross polarization Methods 0.000 description 1
- 239000011549 crystallization solution Substances 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 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 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 238000002050 diffraction method Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 125000005553 heteroaryloxy group Chemical group 0.000 description 1
- 125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000005156 substituted alkylene group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005296 thioaryloxy group Chemical group 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D223/16—Benzazepines; Hydrogenated benzazepines
-
- 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
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Epidemiology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Pyrrole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US24965600P | 2000-11-17 | 2000-11-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200303411B true ZA200303411B (en) | 2004-08-02 |
Family
ID=22944436
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200303411A ZA200303411B (en) | 2000-11-17 | 2003-05-02 | Lactam compound. |
Country Status (33)
| Country | Link |
|---|---|
| US (1) | US20040248878A1 (fr) |
| EP (1) | EP1353910B1 (fr) |
| JP (1) | JP4116431B2 (fr) |
| KR (1) | KR20030045194A (fr) |
| CN (2) | CN100516047C (fr) |
| AR (1) | AR031356A1 (fr) |
| AT (1) | ATE362919T1 (fr) |
| AU (2) | AU2002224321B2 (fr) |
| BR (1) | BR0115424A (fr) |
| CA (1) | CA2425497C (fr) |
| CY (1) | CY1106682T1 (fr) |
| CZ (1) | CZ20031340A3 (fr) |
| DE (1) | DE60128587T2 (fr) |
| DK (1) | DK1353910T3 (fr) |
| DZ (1) | DZ3454A1 (fr) |
| EA (1) | EA006919B1 (fr) |
| EC (1) | ECSP034598A (fr) |
| ES (1) | ES2286162T3 (fr) |
| HR (1) | HRP20030385A2 (fr) |
| HU (1) | HUP0301862A3 (fr) |
| IL (1) | IL155275A0 (fr) |
| MX (1) | MXPA03004250A (fr) |
| MY (1) | MY141607A (fr) |
| NO (1) | NO325217B1 (fr) |
| PE (1) | PE20020798A1 (fr) |
| PL (1) | PL211018B1 (fr) |
| PT (1) | PT1353910E (fr) |
| SK (1) | SK287794B6 (fr) |
| SV (1) | SV2003000741A (fr) |
| TW (1) | TWI235151B (fr) |
| UA (1) | UA77165C2 (fr) |
| WO (1) | WO2002040451A2 (fr) |
| ZA (1) | ZA200303411B (fr) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA74849C2 (en) * | 2000-11-17 | 2006-02-15 | Lilly Co Eli | Lactam |
| ES2401216T3 (es) | 2002-12-20 | 2013-04-17 | Glaxo Group Limited | Nuevos derivados de benzazepina |
| ATE374766T1 (de) | 2003-01-14 | 2007-10-15 | Arena Pharm Inc | 1,2,3-trisubstituierte aryl- und heteroarylderivate als modulatoren des metabolismus zur vorbeugung und behandlung von metabolismus-bedingten krankheiten wie diabetes oder hyperglykämie |
| EP1867636B1 (fr) | 2005-04-08 | 2013-06-05 | Daiichi Sankyo Company, Limited | Dérivé de pyridylméthylsulfone |
| EP1985615A4 (fr) | 2006-01-31 | 2011-12-14 | Api Corp | Procédé de production de benzazépinone |
| TW200920362A (en) | 2007-09-11 | 2009-05-16 | Daiichi Sankyo Co Ltd | Alkylsulfone derivatives |
| FR2932800B1 (fr) * | 2008-06-20 | 2015-02-20 | Servier Lab | Nouveau procede de synthese de la 7,8-dimethoxy-1,3-dihydro- 2h-3-benzazepin-2-one, et application a la synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable |
| CA2812061A1 (fr) | 2010-09-22 | 2012-03-29 | Arena Pharmaceuticals, Inc. | Modulateurs du recepteur gpr119 et traitement des troubles qui lui sont lies |
| KR101899014B1 (ko) | 2012-01-06 | 2018-09-17 | 삼성전자주식회사 | 비엘디씨 모터의 제어 장치 및 그 방법 |
| CN102690231B (zh) * | 2012-04-11 | 2014-07-09 | 南京友杰医药科技有限公司 | 治疗阿尔茨海默病潜在药物司马西特的合成方法 |
| US20160067306A1 (en) | 2013-04-19 | 2016-03-10 | National University Corporation Hokkaido University | Treatment agent for cognitive impairment induced by amyloid beta-protein, therapeutic agent for alzheimer's disease, and treatment method and pathological analysis method related to these |
| CN107405332A (zh) | 2015-01-06 | 2017-11-28 | 艾尼纳制药公司 | 治疗与s1p1受体有关的病症的方法 |
| CA3002551A1 (fr) | 2015-06-22 | 2016-12-29 | Arena Pharmaceuticals, Inc. | Sel cristallin de l-arginine de (r)(7-(4-cyclopentyle-3-(trifluoromethyle)benzyloxy)-1,2,3,4-tetrahydrocyclo-penta[b]indol-3-yl)acide acetique(compose 1) aux fins d'utilisation contre les troubles associes au recepteur s1p1 |
| CN110520124A (zh) | 2017-02-16 | 2019-11-29 | 艾尼纳制药公司 | 用于治疗原发性胆汁性胆管炎的化合物和方法 |
| WO2021195362A1 (fr) | 2020-03-26 | 2021-09-30 | Seagen Inc. | Méthodes de traitement du myélome multiple |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EA002100B1 (ru) * | 1996-12-23 | 2001-12-24 | Элан Фармасьютикалз, Инк. | ЦИКЛОАЛКИЛЬНЫЕ СОЕДИНЕНИЯ, ЛАКТАМЫ, ЛАКТОНЫ И РОДСТВЕННЫЕ СОЕДИНЕНИЯ, СОДЕРЖАЩИЕ ИХ ФАРМАЦЕВТИЧЕСКИЕ КОМПОЗИЦИИ И СПОСОБЫ ИНГИБИРОВАНИЯ ВЫСВОБОЖДЕНИЯ И/ИЛИ СИНТЕЗА β-АМИЛОИДНОГО ПЕПТИДА С ПОМОЩЬЮ УКАЗАННЫХ СОЕДИНЕНИЙ |
| WO1999067219A1 (fr) * | 1998-06-22 | 1999-12-29 | Elan Pharmaceuticals, Inc. | Composes destines a inhiber la liberation et/ou la synthese du peptide beta-amyloide |
| EP1230220A1 (fr) * | 1999-11-09 | 2002-08-14 | Eli Lilly And Company | COMPOSES CONTENANT DES $g(b)-ACIDES AMINES UTILES POUR INHIBER LA LIBERATION ET/OU LA SYNTHESE DU PEPTIDE $g(b)-AMYLOIDE |
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2001
- 2001-02-11 UA UA2003054406A patent/UA77165C2/uk unknown
- 2001-11-02 SK SK543-2003A patent/SK287794B6/sk not_active IP Right Cessation
- 2001-11-02 AU AU2002224321A patent/AU2002224321B2/en not_active Ceased
- 2001-11-02 BR BR0115424-9A patent/BR0115424A/pt not_active Application Discontinuation
- 2001-11-02 PL PL360991A patent/PL211018B1/pl unknown
- 2001-11-02 CZ CZ20031340A patent/CZ20031340A3/cs unknown
- 2001-11-02 IL IL15527501A patent/IL155275A0/xx unknown
- 2001-11-02 CN CNB018189962A patent/CN100516047C/zh not_active Expired - Fee Related
- 2001-11-02 WO PCT/US2001/027795 patent/WO2002040451A2/fr active IP Right Grant
- 2001-11-02 PT PT01996530T patent/PT1353910E/pt unknown
- 2001-11-02 AT AT01996530T patent/ATE362919T1/de active
- 2001-11-02 EP EP01996530A patent/EP1353910B1/fr not_active Expired - Lifetime
- 2001-11-02 US US10/415,548 patent/US20040248878A1/en not_active Abandoned
- 2001-11-02 HU HU0301862A patent/HUP0301862A3/hu unknown
- 2001-11-02 EA EA200300579A patent/EA006919B1/ru unknown
- 2001-11-02 CN CN200910203885A patent/CN101624372A/zh active Pending
- 2001-11-02 ES ES01996530T patent/ES2286162T3/es not_active Expired - Lifetime
- 2001-11-02 DE DE60128587T patent/DE60128587T2/de not_active Expired - Lifetime
- 2001-11-02 AU AU2432102A patent/AU2432102A/xx active Pending
- 2001-11-02 DZ DZ013454A patent/DZ3454A1/fr active
- 2001-11-02 MX MXPA03004250A patent/MXPA03004250A/es active IP Right Grant
- 2001-11-02 DK DK01996530T patent/DK1353910T3/da active
- 2001-11-02 KR KR10-2003-7006660A patent/KR20030045194A/ko not_active Application Discontinuation
- 2001-11-02 CA CA2425497A patent/CA2425497C/fr not_active Expired - Fee Related
- 2001-11-02 JP JP2002542779A patent/JP4116431B2/ja not_active Expired - Fee Related
- 2001-11-15 TW TW090128351A patent/TWI235151B/zh not_active IP Right Cessation
- 2001-11-15 AR ARP010105339A patent/AR031356A1/es not_active Application Discontinuation
- 2001-11-15 MY MYPI20015251A patent/MY141607A/en unknown
- 2001-11-16 PE PE2001001143A patent/PE20020798A1/es not_active Application Discontinuation
- 2001-11-16 SV SV2001000741A patent/SV2003000741A/es unknown
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2003
- 2003-05-02 ZA ZA200303411A patent/ZA200303411B/en unknown
- 2003-05-13 EC EC2003004598A patent/ECSP034598A/es unknown
- 2003-05-14 HR HR20030385A patent/HRP20030385A2/hr not_active Application Discontinuation
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