CA2541162A1 - Fused lactam compounds - Google Patents

Fused lactam compounds Download PDF

Info

Publication number: CA2541162A1
Authority: CA; Canada
Prior art keywords: hydroxy; group; dihydroquinolin; carbon atoms; groups
Prior art date: 2003-10-08
Legal status (The legal status 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 status listed.): Abandoned

Application number

CA002541162A

Other languages

English (en)

French (fr)

Inventor

Kazuo Ando

Masako Hirota

Makoto Kawai

Hirohisa Shimokawa

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Pfizer Inc

Original Assignee

Individual

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.)

2003-10-08

Filing date

2004-09-27

Publication date

2005-04-21

2004-09-27 Application filed by Individual filed Critical Individual

2005-04-21 Publication of CA2541162A1 publication Critical patent/CA2541162A1/en

Status Abandoned legal-status Critical Current

Links

-1 lactam compounds Chemical class 0.000 title claims description 158
150000001875 compounds Chemical class 0.000 claims abstract description 206
208000002193 Pain Diseases 0.000 claims abstract description 52
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 52
230000036407 pain Effects 0.000 claims abstract description 48
150000003839 salts Chemical class 0.000 claims abstract description 39
125000000217 alkyl group Chemical group 0.000 claims abstract description 29
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 26
125000001424 substituent group Chemical group 0.000 claims abstract description 22
201000010099 disease Diseases 0.000 claims abstract description 20
238000011282 treatment Methods 0.000 claims abstract description 19
108010038912 Retinoid X Receptors Proteins 0.000 claims abstract description 18
125000003118 aryl group Chemical group 0.000 claims abstract description 13
150000002148 esters Chemical class 0.000 claims abstract description 13
125000001072 heteroaryl group Chemical group 0.000 claims abstract description 11
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 9
208000019695 Migraine disease Diseases 0.000 claims abstract description 6
208000018737 Parkinson disease Diseases 0.000 claims abstract description 6
206010027599 migraine Diseases 0.000 claims abstract description 6
208000024827 Alzheimer disease Diseases 0.000 claims abstract description 5
208000019901 Anxiety disease Diseases 0.000 claims abstract description 5
230000036506 anxiety Effects 0.000 claims abstract description 5
102000034527 Retinoid X Receptors Human genes 0.000 claims abstract 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 19
239000003814 drug Substances 0.000 claims description 17
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 16
208000014674 injury Diseases 0.000 claims description 16
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 description 14
125000005843 halogen group Chemical group 0.000 claims description 14
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
230000006378 damage Effects 0.000 claims description 13
208000027418 Wounds and injury Diseases 0.000 claims description 12
125000003545 alkoxy group Chemical group 0.000 claims description 10
230000001684 chronic effect Effects 0.000 claims description 9
239000008194 pharmaceutical composition Substances 0.000 claims description 8
241000725303 Human immunodeficiency virus Species 0.000 claims description 7
125000003384 isochromanyl group Chemical group C1(OCCC2=CC=CC=C12)* 0.000 claims description 7
230000004770 neurodegeneration Effects 0.000 claims description 7
125000004430 oxygen atom Chemical group O* 0.000 claims description 7
125000004076 pyridyl group Chemical group 0.000 claims description 7
125000000335 thiazolyl group Chemical group 0.000 claims description 7
206010028980 Neoplasm Diseases 0.000 claims description 6
125000004414 alkyl thio group Chemical group 0.000 claims description 6
206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 6
125000004429 atom Chemical group 0.000 claims description 6
208000002551 irritable bowel syndrome Diseases 0.000 claims description 6
208000015122 neurodegenerative disease Diseases 0.000 claims description 6
125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims description 5
125000005842 heteroatom Chemical group 0.000 claims description 5
125000005956 isoquinolyl group Chemical group 0.000 claims description 5
125000001786 isothiazolyl group Chemical group 0.000 claims description 5
125000002971 oxazolyl group Chemical group 0.000 claims description 5
125000000168 pyrrolyl group Chemical group 0.000 claims description 5
125000005493 quinolyl group Chemical group 0.000 claims description 5
125000004434 sulfur atom Chemical group 0.000 claims description 5
XBFIEFZLLOTBAK-UHFFFAOYSA-N 7-[1-hydroxy-2-[4-hydroxy-4-(6-methoxypyridin-3-yl)piperidin-1-yl]ethyl]-1,3,4,5-tetrahydro-1-benzazepin-2-one Chemical compound C1=NC(OC)=CC=C1C1(O)CCN(CC(O)C=2C=C3CCCC(=O)NC3=CC=2)CC1 XBFIEFZLLOTBAK-UHFFFAOYSA-N 0.000 claims description 4
208000007848 Alcoholism Diseases 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 4
206010015037 epilepsy Diseases 0.000 claims description 4
229910052731 fluorine Chemical group 0.000 claims description 4
125000001153 fluoro group Chemical group F* 0.000 claims description 4
125000000842 isoxazolyl group Chemical group 0.000 claims description 4
125000006413 ring segment Chemical group 0.000 claims description 4
206010002091 Anaesthesia Diseases 0.000 claims description 3
208000032116 Autoimmune Experimental Encephalomyelitis Diseases 0.000 claims description 3
206010010904 Convulsion Diseases 0.000 claims description 3
206010013654 Drug abuse Diseases 0.000 claims description 3
208000012661 Dyskinesia Diseases 0.000 claims description 3
208000010412 Glaucoma Diseases 0.000 claims description 3
208000023105 Huntington disease Diseases 0.000 claims description 3
208000009205 Tinnitus Diseases 0.000 claims description 3
206010001584 alcohol abuse Diseases 0.000 claims description 3
208000025746 alcohol use disease Diseases 0.000 claims description 3
125000002947 alkylene group Chemical group 0.000 claims description 3
208000029028 brain injury Diseases 0.000 claims description 3
230000006999 cognitive decline Effects 0.000 claims description 3
208000010877 cognitive disease Diseases 0.000 claims description 3
230000001537 neural effect Effects 0.000 claims description 3
125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
201000000980 schizophrenia Diseases 0.000 claims description 3
208000011117 substance-related disease Diseases 0.000 claims description 3
231100000886 tinnitus Toxicity 0.000 claims description 3
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
QZQMDHNAPKQIDU-UHFFFAOYSA-N 5-fluoro-6-[1-hydroxy-2-[4-hydroxy-4-[4-(methoxymethyl)phenyl]piperidin-1-yl]ethyl]-3,4-dihydro-1h-quinolin-2-one Chemical compound C1=CC(COC)=CC=C1C1(O)CCN(CC(O)C=2C(=C3CCC(=O)NC3=CC=2)F)CC1 QZQMDHNAPKQIDU-UHFFFAOYSA-N 0.000 claims 2
YTLSKXXSEGIYIY-UHFFFAOYSA-N 6-[1-hydroxy-2-[4-hydroxy-4-(4-methylpyridin-2-yl)piperidin-1-yl]ethyl]-3,4-dihydro-1h-quinolin-2-one Chemical compound CC1=CC=NC(C2(O)CCN(CC(O)C=3C=C4CCC(=O)NC4=CC=3)CC2)=C1 YTLSKXXSEGIYIY-UHFFFAOYSA-N 0.000 claims 2
GMAPGPMRNUCCQF-UHFFFAOYSA-N 6-[1-hydroxy-2-[4-hydroxy-4-(6-methoxypyridin-3-yl)piperidin-1-yl]ethyl]-3,4-dihydro-1h-quinolin-2-one Chemical compound C1=NC(OC)=CC=C1C1(O)CCN(CC(O)C=2C=C3CCC(=O)NC3=CC=2)CC1 GMAPGPMRNUCCQF-UHFFFAOYSA-N 0.000 claims 2
MWKDTYNUIDDMRL-UHFFFAOYSA-N 6-[1-hydroxy-2-[4-hydroxy-4-[4-(methoxymethyl)phenyl]piperidin-1-yl]ethyl]-3,4-dihydro-1h-quinolin-2-one Chemical compound C1=CC(COC)=CC=C1C1(O)CCN(CC(O)C=2C=C3CCC(=O)NC3=CC=2)CC1 MWKDTYNUIDDMRL-UHFFFAOYSA-N 0.000 claims 2
WBUNDLKSFHEQPC-UHFFFAOYSA-N 6-[2-[4-(3,4-dihydro-1h-isochromen-7-yl)-4-hydroxypiperidin-1-yl]-1-hydroxyethyl]-3,4-dihydro-1h-quinolin-2-one Chemical compound N1C(=O)CCC2=CC(C(CN3CCC(O)(CC3)C=3C=C4COCCC4=CC=3)O)=CC=C21 WBUNDLKSFHEQPC-UHFFFAOYSA-N 0.000 claims 2
WWZSPEBAKZSJOC-UHFFFAOYSA-N 6-[2-[4-(6-ethoxypyridin-3-yl)-4-hydroxypiperidin-1-yl]-1-hydroxyethyl]-3,4-dihydro-1h-quinolin-2-one Chemical compound C1=NC(OCC)=CC=C1C1(O)CCN(CC(O)C=2C=C3CCC(=O)NC3=CC=2)CC1 WWZSPEBAKZSJOC-UHFFFAOYSA-N 0.000 claims 2
MYZHSFFINAQMQJ-UHFFFAOYSA-N 6-[2-[4-(6-fluoro-5-methoxypyridin-2-yl)-4-hydroxypiperidin-1-yl]-1-hydroxyethyl]-3,4-dihydro-1h-quinolin-2-one Chemical compound N1=C(F)C(OC)=CC=C1C1(O)CCN(CC(O)C=2C=C3CCC(=O)NC3=CC=2)CC1 MYZHSFFINAQMQJ-UHFFFAOYSA-N 0.000 claims 2
WRJWSZYKVRHCDG-UHFFFAOYSA-N 5-fluoro-6-[1-hydroxy-2-[4-hydroxy-4-(6-methoxypyridin-3-yl)piperidin-1-yl]ethyl]-3,4-dihydro-1h-quinolin-2-one Chemical compound C1=NC(OC)=CC=C1C1(O)CCN(CC(O)C=2C(=C3CCC(=O)NC3=CC=2)F)CC1 WRJWSZYKVRHCDG-UHFFFAOYSA-N 0.000 claims 1
BNDZWZNTSWDGBV-UHFFFAOYSA-N 5-fluoro-6-[2-[4-(6-fluoro-5-methoxypyridin-2-yl)-4-hydroxypiperidin-1-yl]-1-hydroxyethyl]-3,4-dihydro-1h-quinolin-2-one Chemical compound N1=C(F)C(OC)=CC=C1C1(O)CCN(CC(O)C=2C(=C3CCC(=O)NC3=CC=2)F)CC1 BNDZWZNTSWDGBV-UHFFFAOYSA-N 0.000 claims 1
ONOSOXBPLHKQCX-UHFFFAOYSA-N 6-[1-hydroxy-2-[4-hydroxy-4-(5-methoxypyridin-2-yl)piperidin-1-yl]ethyl]-3,4-dihydro-1h-quinolin-2-one Chemical compound N1=CC(OC)=CC=C1C1(O)CCN(CC(O)C=2C=C3CCC(=O)NC3=CC=2)CC1 ONOSOXBPLHKQCX-UHFFFAOYSA-N 0.000 claims 1
DLAYQZIMGJJXRD-UHFFFAOYSA-N 6-[2-[4-(2-ethoxy-1,3-thiazol-5-yl)-4-hydroxypiperidin-1-yl]-1-hydroxyethyl]-3,4-dihydro-1h-quinolin-2-one Chemical compound S1C(OCC)=NC=C1C1(O)CCN(CC(O)C=2C=C3CCC(=O)NC3=CC=2)CC1 DLAYQZIMGJJXRD-UHFFFAOYSA-N 0.000 claims 1
YSKHYNVMAUHRPB-UHFFFAOYSA-N 6-[2-[4-(3,4-dihydro-1h-isochromen-7-yl)-4-hydroxypiperidin-1-yl]-1-hydroxyethyl]-5-fluoro-3,4-dihydro-1h-quinolin-2-one Chemical compound N1C(=O)CCC2=C(F)C(C(CN3CCC(O)(CC3)C=3C=C4COCCC4=CC=3)O)=CC=C21 YSKHYNVMAUHRPB-UHFFFAOYSA-N 0.000 claims 1
YODIRHFCLBWKHW-UHFFFAOYSA-N 6-[2-[4-(6-chloro-5-methoxypyridin-2-yl)-4-hydroxypiperidin-1-yl]-1-hydroxyethyl]-3,4-dihydro-1h-quinolin-2-one Chemical compound N1=C(Cl)C(OC)=CC=C1C1(O)CCN(CC(O)C=2C=C3CCC(=O)NC3=CC=2)CC1 YODIRHFCLBWKHW-UHFFFAOYSA-N 0.000 claims 1
SEWWPGGETPDKKX-UHFFFAOYSA-N 6-[2-[4-[5-(dimethylamino)-6-fluoropyridin-2-yl]-4-hydroxypiperidin-1-yl]-1-hydroxyethyl]-3,4-dihydro-1h-quinolin-2-one Chemical compound N1=C(F)C(N(C)C)=CC=C1C1(O)CCN(CC(O)C=2C=C3CCC(=O)NC3=CC=2)CC1 SEWWPGGETPDKKX-UHFFFAOYSA-N 0.000 claims 1
208000006011 Stroke Diseases 0.000 abstract description 3
229910052736 halogen Inorganic materials 0.000 abstract description 3
150000002367 halogens Chemical class 0.000 abstract description 3
208000030886 Traumatic Brain injury Diseases 0.000 abstract description 2
230000009529 traumatic brain injury Effects 0.000 abstract description 2
239000000203 mixture Substances 0.000 description 114
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 99
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 93
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 86
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 76
238000005160 1H NMR spectroscopy Methods 0.000 description 75
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 66
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 66
239000000243 solution Substances 0.000 description 66
239000007787 solid Substances 0.000 description 64
238000000034 method Methods 0.000 description 57
238000006243 chemical reaction Methods 0.000 description 46
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 44
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 39
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 39
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 38
235000019441 ethanol Nutrition 0.000 description 37
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 36
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 35
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 29
210000004027 cell Anatomy 0.000 description 29
239000000725 suspension Substances 0.000 description 29
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
238000009472 formulation Methods 0.000 description 27
239000002904 solvent Substances 0.000 description 22
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 description 19
239000012044 organic layer Substances 0.000 description 19
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 19
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
239000002244 precipitate Substances 0.000 description 18
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
239000000843 powder Substances 0.000 description 15
125000006239 protecting group Chemical group 0.000 description 15
102100022630 Glutamate receptor ionotropic, NMDA 2B Human genes 0.000 description 14
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 13
239000003153 chemical reaction reagent Substances 0.000 description 13
230000002829 reductive effect Effects 0.000 description 13
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 12
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
229910052802 copper Inorganic materials 0.000 description 12
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 12
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 12
101150041968 CDC13 gene Proteins 0.000 description 11
101001047090 Homo sapiens Potassium voltage-gated channel subfamily H member 2 Proteins 0.000 description 11
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 11
239000002253 acid Substances 0.000 description 11
239000010949 copper Substances 0.000 description 11
238000001914 filtration Methods 0.000 description 11
239000003921 oil Substances 0.000 description 11
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
239000005557 antagonist Substances 0.000 description 10
239000003054 catalyst Substances 0.000 description 10
229940079593 drug Drugs 0.000 description 10
239000012442 inert solvent Substances 0.000 description 10
239000000741 silica gel Substances 0.000 description 10
229910002027 silica gel Inorganic materials 0.000 description 10
229960001866 silicon dioxide Drugs 0.000 description 10
239000012279 sodium borohydride Substances 0.000 description 10
229910000033 sodium borohydride Inorganic materials 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
229910000041 hydrogen chloride Inorganic materials 0.000 description 9
239000012528 membrane Substances 0.000 description 9
229910052757 nitrogen Inorganic materials 0.000 description 9
210000000929 nociceptor Anatomy 0.000 description 9
108091008700 nociceptors Proteins 0.000 description 9
238000012360 testing method Methods 0.000 description 9
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
238000003556 assay Methods 0.000 description 8
229910052739 hydrogen Inorganic materials 0.000 description 8
239000001257 hydrogen Substances 0.000 description 8
208000004454 Hyperalgesia Diseases 0.000 description 7
125000005129 aryl carbonyl group Chemical group 0.000 description 7
239000002585 base Substances 0.000 description 7
239000012267 brine Substances 0.000 description 7
238000004587 chromatography analysis Methods 0.000 description 7
238000001816 cooling Methods 0.000 description 7
239000012043 crude product Substances 0.000 description 7
229960002994 dofetilide Drugs 0.000 description 7
230000000694 effects Effects 0.000 description 7
238000002474 experimental method Methods 0.000 description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
208000004296 neuralgia Diseases 0.000 description 7
208000021722 neuropathic pain Diseases 0.000 description 7
239000000546 pharmaceutical excipient Substances 0.000 description 7
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108020003175 receptors Proteins 0.000 description 7
238000001953 recrystallisation Methods 0.000 description 7
230000004044 response Effects 0.000 description 7
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 7
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 7
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 6
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UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 6
102100022807 Potassium voltage-gated channel subfamily H member 2 Human genes 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
230000027455 binding Effects 0.000 description 6
208000035475 disorder Diseases 0.000 description 6
IXTMWRCNAAVVAI-UHFFFAOYSA-N dofetilide Chemical compound C=1C=C(NS(C)(=O)=O)C=CC=1CCN(C)CCOC1=CC=C(NS(C)(=O)=O)C=C1 IXTMWRCNAAVVAI-UHFFFAOYSA-N 0.000 description 6
150000002170 ethers Chemical class 0.000 description 6
230000002401 inhibitory effect Effects 0.000 description 6
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
229910052751 metal Inorganic materials 0.000 description 6
239000002184 metal Substances 0.000 description 6
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
229910000027 potassium carbonate Inorganic materials 0.000 description 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
229940002612 prodrug Drugs 0.000 description 6
239000000651 prodrug Substances 0.000 description 6
238000000746 purification Methods 0.000 description 6
230000035484 reaction time Effects 0.000 description 6
230000009467 reduction Effects 0.000 description 6
208000024891 symptom Diseases 0.000 description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
208000022559 Inflammatory bowel disease Diseases 0.000 description 5
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 5
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
239000012298 atmosphere Substances 0.000 description 5
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Classifications

- 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
- C07D401/06—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 carbon chain containing only aliphatic carbon atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- 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
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P25/06—Antimigraine agents
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P25/08—Antiepileptics; Anticonvulsants
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- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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- 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
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- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/32—Alcohol-abuse
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P27/16—Otologicals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents

Landscapes

Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Psychiatry (AREA)
Addiction (AREA)
Pain & Pain Management (AREA)
Psychology (AREA)
Ophthalmology & Optometry (AREA)
Hospice & Palliative Care (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

CA002541162A 2003-10-08 2004-09-27 Fused lactam compounds Abandoned CA2541162A1 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US50967003P	2003-10-08	2003-10-08
US60/509,670		2003-10-08
PCT/IB2004/003125 WO2005035523A1 (en)	2003-10-08	2004-09-27	Fused lactam compounds

Publications (1)

Publication Number	Publication Date
CA2541162A1 true CA2541162A1 (en)	2005-04-21

Family

ID=34435007

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002541162A Abandoned CA2541162A1 (en)	2003-10-08	2004-09-27	Fused lactam compounds

Country Status (6)

Country	Link
EP (1)	EP1673367A1 (es)
JP (1)	JP2007508288A (es)
BR (1)	BRPI0415113A (es)
CA (1)	CA2541162A1 (es)
MX (1)	MXPA06003748A (es)
WO (1)	WO2005035523A1 (es)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2005097782A1 (ja) *	2004-04-07	2005-10-20	Kyowa Hakko Kogyo Co., Ltd.	ピペリジン誘導体
CN103002893B (zh)	2010-07-30	2017-05-10	东丽株式会社	神经障碍性疼痛的治疗药或预防药
EP2838530B1 (en)	2012-04-20	2017-04-05	UCB Biopharma SPRL	Methods for treating parkinson's disease
US10154988B2 (en)	2012-11-14	2018-12-18	The Johns Hopkins University	Methods and compositions for treating schizophrenia
WO2014144801A1 (en)	2013-03-15	2014-09-18	Agenebio Inc.	Methods and compositions for improving cognitive function
WO2014144663A1 (en)	2013-03-15	2014-09-18	The Johns Hopkins University	Methods and compositions for improving cognitive function
US9221796B2 (en)	2014-01-09	2015-12-29	Bristol-Myers Squibb Company	Selective NR2B antagonists
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2004
- 2004-09-27 EP EP04769480A patent/EP1673367A1/en not_active Withdrawn
- 2004-09-27 JP JP2006530731A patent/JP2007508288A/ja not_active Withdrawn
- 2004-09-27 WO PCT/IB2004/003125 patent/WO2005035523A1/en not_active Application Discontinuation
- 2004-09-27 CA CA002541162A patent/CA2541162A1/en not_active Abandoned
- 2004-09-27 MX MXPA06003748A patent/MXPA06003748A/es unknown
- 2004-09-27 BR BRPI0415113-5A patent/BRPI0415113A/pt not_active IP Right Cessation

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WO2005035523A1 (en)	2005-04-21
MXPA06003748A (es)	2006-06-14
EP1673367A1 (en)	2006-06-28
BRPI0415113A (pt)	2006-11-28
JP2007508288A (ja)	2007-04-05

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