BG107375A - Бициклени циклохексиламини и тяхното приложение като антагонисти на nmda-рецептор - Google Patents

Бициклени циклохексиламини и тяхното приложение като антагонисти на nmda-рецептор Download PDF

Info

Publication number: BG107375A
Authority: BG; Bulgaria
Prior art keywords: mmol; cyclohexyl; benzoxazol; trans; nmr
Prior art date: 2000-05-31

Application number

BG107375A

Other languages

Bulgarian (bg)

English (en)

Inventor

Sham Nikam

Ian Scott

Brian Sherer

Lawrence WISE

Original Assignee

Warner-Lambert Company

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.)

2000-05-31

Filing date

2002-12-11

Publication date

2003-09-30

2002-12-11 Application filed by Warner-Lambert Company filed Critical Warner-Lambert Company

2003-09-30 Publication of BG107375A publication Critical patent/BG107375A/bg

Links

-1 Bicyclic cyclohexylamines Chemical class 0.000 title description 166
229940127523 NMDA Receptor Antagonists Drugs 0.000 title description 3
150000003839 salts Chemical class 0.000 claims abstract description 27
150000003946 cyclohexylamines Chemical class 0.000 claims abstract description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 53
125000000217 alkyl group Chemical group 0.000 claims description 46
239000001257 hydrogen Substances 0.000 claims description 44
125000001424 substituent group Chemical group 0.000 claims description 32
125000003710 aryl alkyl group Chemical group 0.000 claims description 22
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
125000004103 aminoalkyl group Chemical group 0.000 claims description 20
125000001072 heteroaryl group Chemical group 0.000 claims description 16
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 15
125000004446 heteroarylalkyl group Chemical group 0.000 claims description 14
125000002619 bicyclic group Chemical group 0.000 claims description 9
229910052740 iodine Inorganic materials 0.000 claims description 9
125000003118 aryl group Chemical group 0.000 claims description 8
125000004429 atom Chemical group 0.000 claims description 8
229910052794 bromium Inorganic materials 0.000 claims description 8
125000000753 cycloalkyl group Chemical group 0.000 claims description 8
125000004946 alkenylalkyl group Chemical group 0.000 claims description 7
229910052801 chlorine Inorganic materials 0.000 claims description 7
229910052731 fluorine Inorganic materials 0.000 claims description 7
125000004001 thioalkyl group Chemical group 0.000 claims description 7
125000004181 carboxyalkyl group Chemical group 0.000 claims description 6
125000006575 electron-withdrawing group Chemical group 0.000 claims description 6
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 6
125000005842 heteroatom Chemical group 0.000 claims description 5
229910052717 sulfur Inorganic materials 0.000 claims description 5
229910052760 oxygen Inorganic materials 0.000 claims description 4
150000001875 compounds Chemical class 0.000 abstract description 57
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201000006474 Brain Ischemia Diseases 0.000 abstract description 4
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208000010496 Heart Arrest Diseases 0.000 abstract description 2
230000002490 cerebral effect Effects 0.000 abstract description 2
208000023516 stroke disease Diseases 0.000 abstract 1
208000019553 vascular disease Diseases 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 270
238000000034 method Methods 0.000 description 206
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 144
239000000243 solution Substances 0.000 description 110
239000007787 solid Substances 0.000 description 95
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 93
239000011541 reaction mixture Substances 0.000 description 75
230000002829 reductive effect Effects 0.000 description 72
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 68
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 60
239000000460 chlorine Substances 0.000 description 59
238000004458 analytical method Methods 0.000 description 58
125000006308 propyl amino group Chemical group 0.000 description 58
150000003840 hydrochlorides Chemical class 0.000 description 57
238000004128 high performance liquid chromatography Methods 0.000 description 55
239000000203 mixture Substances 0.000 description 55
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 50
ASSKVPFEZFQQNQ-UHFFFAOYSA-N Benzoxazolone Natural products C1=CC=C2OC(O)=NC2=C1 ASSKVPFEZFQQNQ-UHFFFAOYSA-N 0.000 description 49
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238000000746 purification Methods 0.000 description 43
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VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 38
150000002576 ketones Chemical class 0.000 description 37
238000006243 chemical reaction Methods 0.000 description 36
238000003818 flash chromatography Methods 0.000 description 36
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 34
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 34
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238000002360 preparation method Methods 0.000 description 21
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125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 15
239000002904 solvent Substances 0.000 description 15
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239000012044 organic layer Substances 0.000 description 11
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239000003826 tablet Substances 0.000 description 11
WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 10
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 10
WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 10
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 10
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 10
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
239000012298 atmosphere Substances 0.000 description 10
150000001540 azides Chemical class 0.000 description 10
239000000872 buffer Substances 0.000 description 10
125000004432 carbon atom Chemical group C* 0.000 description 10
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238000005984 hydrogenation reaction Methods 0.000 description 10
229960003998 ifenprodil Drugs 0.000 description 10
WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 10
239000002808 molecular sieve Substances 0.000 description 10
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 10
238000003786 synthesis reaction Methods 0.000 description 10
DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 9
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102000014649 NMDA glutamate receptor activity proteins Human genes 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
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201000010099 disease Diseases 0.000 description 9
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 9
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229910052736 halogen Inorganic materials 0.000 description 9
150000002367 halogens Chemical class 0.000 description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
125000000547 substituted alkyl group Chemical group 0.000 description 9
125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 description 8
MLACDGUOKDOLGC-UHFFFAOYSA-N 5-(2-aminoethyl)benzene-1,2,4-triol;hydron;bromide Chemical compound Br.NCCC1=CC(O)=C(O)C=C1O MLACDGUOKDOLGC-UHFFFAOYSA-N 0.000 description 8
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RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 8
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
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125000001188 haloalkyl group Chemical group 0.000 description 8
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QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 7
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229910052786 argon Inorganic materials 0.000 description 7
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125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 7
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HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
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- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
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- 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
- C07D413/02—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
- 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
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General Chemical & Material Sciences (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Psychiatry (AREA)
Ophthalmology & Optometry (AREA)
Pain & Pain Management (AREA)
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Urology & Nephrology (AREA)
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Endocrinology (AREA)
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Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Medicines Containing Material From Animals Or Micro-Organisms (AREA)
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BG107375A 2000-05-31 2002-12-11 Бициклени циклохексиламини и тяхното приложение като антагонисти на nmda-рецептор BG107375A (bg)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US20824100P	2000-05-31	2000-05-31
PCT/US2001/014763 WO2001092239A1 (en)	2000-05-31	2001-05-08	Biciclic cyclohexylamines and their use as nmda receptor antogonists

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BG107375A true BG107375A (bg)	2003-09-30

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US (1)	US6794402B2 (xx)
EP (1)	EP1286975B1 (xx)
JP (1)	JP2003535083A (xx)
KR (1)	KR20030007797A (xx)
CN (1)	CN1438996A (xx)
AP (1)	AP2002002697A0 (xx)
AT (1)	ATE302763T1 (xx)
AU (1)	AU2001259618A1 (xx)
BG (1)	BG107375A (xx)
BR (1)	BR0111301A (xx)
CA (1)	CA2409006A1 (xx)
DE (1)	DE60112924T2 (xx)
DZ (1)	DZ3361A1 (xx)
EA (1)	EA200201158A1 (xx)
EE (1)	EE200200667A (xx)
ES (1)	ES2245985T3 (xx)
HR (1)	HRP20021018A2 (xx)
HU (1)	HUP0302323A2 (xx)
IL (1)	IL153170A0 (xx)
IS (1)	IS6625A (xx)
MA (1)	MA26907A1 (xx)
MX (1)	MXPA02011926A (xx)
NO (1)	NO20025762L (xx)
OA (1)	OA12275A (xx)
PL (1)	PL359260A1 (xx)
SK (1)	SK16632002A3 (xx)
WO (1)	WO2001092239A1 (xx)
ZA (1)	ZA200209325B (xx)

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2001
- 2001-05-08 EE EEP200200667A patent/EE200200667A/xx unknown
- 2001-05-08 DE DE60112924T patent/DE60112924T2/de not_active Expired - Fee Related
- 2001-05-08 DZ DZ013361A patent/DZ3361A1/fr active
- 2001-05-08 AT AT01933173T patent/ATE302763T1/de not_active IP Right Cessation
- 2001-05-08 CN CN01811676A patent/CN1438996A/zh active Pending
- 2001-05-08 OA OA1200200358A patent/OA12275A/en unknown
- 2001-05-08 EA EA200201158A patent/EA200201158A1/ru unknown
- 2001-05-08 SK SK1663-2002A patent/SK16632002A3/sk not_active Application Discontinuation
- 2001-05-08 ES ES01933173T patent/ES2245985T3/es not_active Expired - Lifetime
- 2001-05-08 PL PL01359260A patent/PL359260A1/xx not_active Application Discontinuation
- 2001-05-08 AP APAP/P/2002/002697A patent/AP2002002697A0/en unknown
- 2001-05-08 BR BR0111301-1A patent/BR0111301A/pt not_active IP Right Cessation
- 2001-05-08 EP EP01933173A patent/EP1286975B1/en not_active Expired - Lifetime
- 2001-05-08 KR KR1020027016301A patent/KR20030007797A/ko not_active Withdrawn
- 2001-05-08 HR HR20021018A patent/HRP20021018A2/hr not_active Application Discontinuation
- 2001-05-08 US US10/276,054 patent/US6794402B2/en not_active Expired - Fee Related
- 2001-05-08 CA CA002409006A patent/CA2409006A1/en not_active Abandoned
- 2001-05-08 IL IL15317001A patent/IL153170A0/xx unknown
- 2001-05-08 HU HU0302323A patent/HUP0302323A2/hu unknown
- 2001-05-08 JP JP2002500853A patent/JP2003535083A/ja active Pending
- 2001-05-08 WO PCT/US2001/014763 patent/WO2001092239A1/en not_active Ceased
- 2001-05-08 AU AU2001259618A patent/AU2001259618A1/en not_active Abandoned
- 2001-05-08 MX MXPA02011926A patent/MXPA02011926A/es active IP Right Grant
2002
- 2002-11-15 ZA ZA200209325A patent/ZA200209325B/en unknown
- 2002-11-18 IS IS6625A patent/IS6625A/is unknown
- 2002-11-27 MA MA26924A patent/MA26907A1/fr unknown
- 2002-11-29 NO NO20025762A patent/NO20025762L/no not_active Application Discontinuation
- 2002-12-11 BG BG107375A patent/BG107375A/bg unknown

Also Published As

Publication number	Publication date
ATE302763T1 (de)	2005-09-15
EE200200667A (et)	2004-06-15
HRP20021018A2 (en)	2004-02-29
SK16632002A3 (sk)	2003-08-05
DE60112924D1 (de)	2005-09-29
PL359260A1 (en)	2004-08-23
BR0111301A (pt)	2003-06-10
US20030236252A1 (en)	2003-12-25
HUP0302323A2 (hu)	2003-10-28
OA12275A (en)	2003-12-11
ZA200209325B (en)	2004-02-16
DE60112924T2 (de)	2006-03-16
MXPA02011926A (es)	2003-04-22
CN1438996A (zh)	2003-08-27
ES2245985T3 (es)	2006-02-01
WO2001092239A1 (en)	2001-12-06
KR20030007797A (ko)	2003-01-23
EP1286975B1 (en)	2005-08-24
NO20025762L (no)	2003-01-09
DZ3361A1 (fr)	2001-12-06
EA200201158A1 (ru)	2003-04-24
EP1286975A1 (en)	2003-03-05
CA2409006A1 (en)	2001-12-06
US6794402B2 (en)	2004-09-21
NO20025762D0 (no)	2002-11-29
MA26907A1 (fr)	2004-12-20
AP2002002697A0 (en)	2002-12-31
IL153170A0 (en)	2003-06-24
JP2003535083A (ja)	2003-11-25
IS6625A (is)	2002-11-18
AU2001259618A1 (en)	2001-12-11

Publication	Publication Date	Title
BG107375A (bg)	2003-09-30	Бициклени циклохексиламини и тяхното приложение като антагонисти на nmda-рецептор
US6780864B1 (en)	2004-08-24	Piperazine and piperidine compounds
US6919377B2 (en)	2005-07-19	Cyclohexylamine derivative as subtype selective NMDA receptor antagonists
WO1998044922A1 (en)	1998-10-15	Somatostatin agonists
EP1292581B1 (en)	2005-08-10	Bicyclic cyclohexylamines and their use as nmda receptor antagonists
US6765022B2 (en)	2004-07-20	Cyclohexylamine derivatives as subtype selective nmda receptor antagonists
CA2436699A1 (en)	2002-06-27	Piperidine derivatives as subtype selective n-methyl-d-aspartate antagonists
US6828341B2 (en)	2004-12-07	Cyclohexylamine derivatives as subtype selective N-Methyl-D-Aspartate antagonists