HRP20000520A2 - 1,2,4,5-TETRADYDRO-BENZO/d/AZEPINES - Google Patents

1,2,4,5-TETRADYDRO-BENZO/d/AZEPINES

Info

Publication number: HRP20000520A2
Authority: HR; Croatia
Prior art keywords: chr; tetrahydro; benzo; azepin; carbonitrile
Prior art date: 1999-08-06

Application number

HR20000520A

Other languages

English (en)

Croatian (hr)

Inventor

Adam Geo

Alfred Binggeli

Hans-Peter Maerki

Vincent Mutel

Maurice Wilhelm

Wolfgang Wostl

Original Assignee

Hoffmann La Roche

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.)

1999-08-06

Filing date

2000-08-02

Publication date

2001-06-30

2000-08-02 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

2001-06-30 Publication of HRP20000520A2 publication Critical patent/HRP20000520A2/hr

Links

150000001538 azepines Chemical class 0.000 title 1
238000000034 method Methods 0.000 claims description 207
150000001875 compounds Chemical class 0.000 claims description 140
125000000217 alkyl group Chemical group 0.000 claims description 72
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 58
-1 or -OR Chemical group 0.000 claims description 58
LDUCGZQCFUMHIK-UHFFFAOYSA-N 2-methyl-5-nitro-6-(1,2,4,5-tetrahydro-3-benzazepin-3-yl)-1h-pyrimidin-4-one Chemical compound CC1=NC(O)=C([N+]([O-])=O)C(N2CCC3=CC=CC=C3CC2)=N1 LDUCGZQCFUMHIK-UHFFFAOYSA-N 0.000 claims description 38
125000003342 alkenyl group Chemical group 0.000 claims description 30
238000006243 chemical reaction Methods 0.000 claims description 30
125000003545 alkoxy group Chemical group 0.000 claims description 27
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 27
125000004093 cyano group Chemical group *C#N 0.000 claims description 24
150000003839 salts Chemical class 0.000 claims description 24
VXBNIUWMGBUTRT-UHFFFAOYSA-N 4-oxo-6-(1,2,4,5-tetrahydro-3-benzazepin-3-yl)-1h-pyrimidine-5-carbonitrile Chemical compound O=C1NC=NC(N2CCC3=CC=CC=C3CC2)=C1C#N VXBNIUWMGBUTRT-UHFFFAOYSA-N 0.000 claims description 23
229910052739 hydrogen Inorganic materials 0.000 claims description 23
239000001257 hydrogen Substances 0.000 claims description 23
OZQHSVVVDNQSDH-UHFFFAOYSA-N 2-amino-4-oxo-6-(1,2,4,5-tetrahydro-3-benzazepin-3-yl)-1h-pyrimidine-5-carbonitrile Chemical compound O=C1NC(N)=NC(N2CCC3=CC=CC=C3CC2)=C1C#N OZQHSVVVDNQSDH-UHFFFAOYSA-N 0.000 claims description 21
125000000524 functional group Chemical group 0.000 claims description 20
229910052736 halogen Inorganic materials 0.000 claims description 19
150000002367 halogens Chemical class 0.000 claims description 19
150000002431 hydrogen Chemical class 0.000 claims description 18
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
UIMKJXDFYJRFQF-UHFFFAOYSA-N 1-amino-2-methyl-6-oxo-4-(1,2,4,5-tetrahydro-3-benzazepin-3-yl)pyrimidine-5-carbonitrile Chemical compound O=C1N(N)C(C)=NC(N2CCC3=CC=CC=C3CC2)=C1C#N UIMKJXDFYJRFQF-UHFFFAOYSA-N 0.000 claims description 12
238000004519 manufacturing process Methods 0.000 claims description 12
150000003335 secondary amines Chemical class 0.000 claims description 11
125000001424 substituent group Chemical group 0.000 claims description 11
125000004432 carbon atom Chemical group C* 0.000 claims description 10
229910052801 chlorine Inorganic materials 0.000 claims description 10
230000001684 chronic effect Effects 0.000 claims description 10
229940079593 drug Drugs 0.000 claims description 10
239000003814 drug Substances 0.000 claims description 10
208000028017 Psychotic disease Diseases 0.000 claims description 9
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 9
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 8
208000002193 Pain Diseases 0.000 claims description 8
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WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 7
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
239000000460 chlorine Substances 0.000 claims description 7
125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 claims description 7
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
208000012902 Nervous system disease Diseases 0.000 claims description 6
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YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 claims description 6
230000001154 acute effect Effects 0.000 claims description 6
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
229910052794 bromium Inorganic materials 0.000 claims description 6
239000011737 fluorine Substances 0.000 claims description 6
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229930195712 glutamate Natural products 0.000 claims description 6
229910052757 nitrogen Inorganic materials 0.000 claims description 6
230000002265 prevention Effects 0.000 claims description 6
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
229910052722 tritium Inorganic materials 0.000 claims description 6
ADXRSPBNIFDIIL-UHFFFAOYSA-N 2-(2-hydroxyethyl)-4-oxo-6-(1,2,4,5-tetrahydro-3-benzazepin-3-yl)-1h-pyrimidine-5-carbonitrile Chemical compound O=C1NC(CCO)=NC(N2CCC3=CC=CC=C3CC2)=C1C#N ADXRSPBNIFDIIL-UHFFFAOYSA-N 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
208000027089 Parkinsonian disease Diseases 0.000 claims description 5
206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 5
230000027455 binding Effects 0.000 claims description 5
108010014719 metabotropic glutamate receptor type 1 Proteins 0.000 claims description 5
230000001629 suppression Effects 0.000 claims description 5
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
NWUORKWXEPJXQF-UHFFFAOYSA-N 1,2-dimethyl-6-oxo-4-(1,2,4,5-tetrahydro-3-benzazepin-3-yl)pyrimidine-5-carbonitrile Chemical compound O=C1N(C)C(C)=NC(N2CCC3=CC=CC=C3CC2)=C1C#N NWUORKWXEPJXQF-UHFFFAOYSA-N 0.000 claims description 4
NEMPTYBDKRDGHY-UHFFFAOYSA-N 1-(2-hydroxyethyl)-6-oxo-4-(1,2,4,5-tetrahydro-3-benzazepin-3-yl)pyrimidine-5-carbonitrile Chemical compound O=C1N(CCO)C=NC(N2CCC3=CC=CC=C3CC2)=C1C#N NEMPTYBDKRDGHY-UHFFFAOYSA-N 0.000 claims description 4
NBSFMOFDESCFSH-UHFFFAOYSA-N 1-(cyanomethyl)-2-methyl-6-oxo-4-(1,2,4,5-tetrahydro-3-benzazepin-3-yl)pyrimidine-5-carbonitrile Chemical compound O=C1N(CC#N)C(C)=NC(N2CCC3=CC=CC=C3CC2)=C1C#N NBSFMOFDESCFSH-UHFFFAOYSA-N 0.000 claims description 4
UTVWGQDJAYXQQP-UHFFFAOYSA-N 1-(cyclopropylmethyl)-2-methyl-6-oxo-4-(1,2,4,5-tetrahydro-3-benzazepin-3-yl)pyrimidine-5-carbonitrile Chemical compound CC1=NC(N2CCC3=CC=CC=C3CC2)=C(C#N)C(=O)N1CC1CC1 UTVWGQDJAYXQQP-UHFFFAOYSA-N 0.000 claims description 4
AHCLTTILLQXZBY-UHFFFAOYSA-N 1-[2-(dimethylamino)ethyl]-2-methyl-6-oxo-4-(1,2,4,5-tetrahydro-3-benzazepin-3-yl)pyrimidine-5-carbonitrile Chemical compound O=C1N(CCN(C)C)C(C)=NC(N2CCC3=CC=CC=C3CC2)=C1C#N AHCLTTILLQXZBY-UHFFFAOYSA-N 0.000 claims description 4
QNUVWRAGDSGAKX-UHFFFAOYSA-N 1-ethyl-2-methyl-6-oxo-4-(1,2,4,5-tetrahydro-3-benzazepin-3-yl)pyrimidine-5-carbonitrile Chemical compound O=C1N(CC)C(C)=NC(N2CCC3=CC=CC=C3CC2)=C1C#N QNUVWRAGDSGAKX-UHFFFAOYSA-N 0.000 claims description 4
BRJWSWOUTCHPTG-UHFFFAOYSA-N 2-(2-hydroxyethylamino)-4-(1,2,4,5-tetrahydro-3-benzazepin-3-yl)-6-(2,2,2-trifluoroethoxy)pyrimidine-5-carbonitrile Chemical compound OCCNC1=NC(OCC(F)(F)F)=C(C#N)C(N2CCC3=CC=CC=C3CC2)=N1 BRJWSWOUTCHPTG-UHFFFAOYSA-N 0.000 claims description 4
XTWMPGSNYMAJGI-UHFFFAOYSA-N 2-(3-imidazol-1-ylpropylamino)-4-(1,2,4,5-tetrahydro-3-benzazepin-3-yl)-6-(2,2,2-trifluoroethoxy)pyrimidine-5-carbonitrile Chemical compound N=1C(N2CCC3=CC=CC=C3CC2)=C(C#N)C(OCC(F)(F)F)=NC=1NCCCN1C=CN=C1 XTWMPGSNYMAJGI-UHFFFAOYSA-N 0.000 claims description 4
FYCSWLGBFSEWJQ-UHFFFAOYSA-N 2-(3-morpholin-4-ylpropylamino)-4-(1,2,4,5-tetrahydro-3-benzazepin-3-yl)-6-(2,2,2-trifluoroethoxy)pyrimidine-5-carbonitrile Chemical compound N=1C(N2CCC3=CC=CC=C3CC2)=C(C#N)C(OCC(F)(F)F)=NC=1NCCCN1CCOCC1 FYCSWLGBFSEWJQ-UHFFFAOYSA-N 0.000 claims description 4
TUCLALLSSVWYSE-UHFFFAOYSA-N 2-amino-1-ethyl-6-oxo-4-(1,2,4,5-tetrahydro-3-benzazepin-3-yl)pyrimidine-5-carbonitrile Chemical compound O=C1N(CC)C(N)=NC(N2CCC3=CC=CC=C3CC2)=C1C#N TUCLALLSSVWYSE-UHFFFAOYSA-N 0.000 claims description 4
FHGDGVRNAVRKTO-UHFFFAOYSA-N 3-(2-fluoroethyl)-2-methyl-5-nitro-6-(1,2,4,5-tetrahydro-3-benzazepin-3-yl)pyrimidin-4-one Chemical compound O=C1N(CCF)C(C)=NC(N2CCC3=CC=CC=C3CC2)=C1[N+]([O-])=O FHGDGVRNAVRKTO-UHFFFAOYSA-N 0.000 claims description 4
XLYNPVUYKJFZME-UHFFFAOYSA-N 4-oxo-2-(1,2,4,5-tetrahydro-3-benzazepin-3-yl)-7,8,9,10-tetrahydro-6h-pyrimido[1,2-a]azepine-3-carbonitrile Chemical compound C1CC2=CC=CC=C2CCN1C1=C(C#N)C(=O)N2CCCCCC2=N1 XLYNPVUYKJFZME-UHFFFAOYSA-N 0.000 claims description 4
ILQVVUZJQWRAAZ-UHFFFAOYSA-N 6-oxo-1-propan-2-yl-4-(1,2,4,5-tetrahydro-3-benzazepin-3-yl)pyrimidine-5-carbonitrile Chemical compound O=C1N(C(C)C)C=NC(N2CCC3=CC=CC=C3CC2)=C1C#N ILQVVUZJQWRAAZ-UHFFFAOYSA-N 0.000 claims description 4
208000024827 Alzheimer disease Diseases 0.000 claims description 4
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GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
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125000004423 acyloxy group Chemical group 0.000 claims description 4
125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 4
230000029936 alkylation Effects 0.000 claims description 4
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150000002009 diols Chemical class 0.000 description 1
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NDEMNVPZDAFUKN-UHFFFAOYSA-N guanidine;nitric acid Chemical compound NC(N)=N.O[N+]([O-])=O.O[N+]([O-])=O NDEMNVPZDAFUKN-UHFFFAOYSA-N 0.000 description 1
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LGRFSURHDFAFJT-UHFFFAOYSA-N phthalic anhydride Chemical class C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
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229910000105 potassium hydride Inorganic materials 0.000 description 1
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
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XIIOFHFUYBLOLW-UHFFFAOYSA-N selpercatinib Chemical compound OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=NC(=CC=1)N1CC2N(C(C1)C2)CC=1C=NC(=CC=1)OC)(C)C XIIOFHFUYBLOLW-UHFFFAOYSA-N 0.000 description 1
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ZNJHFNUEQDVFCJ-UHFFFAOYSA-M sodium;2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid;hydroxide Chemical compound [OH-].[Na+].OCCN1CCN(CCS(O)(=O)=O)CC1 ZNJHFNUEQDVFCJ-UHFFFAOYSA-M 0.000 description 1
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FZMZNAWBMQKJRL-UHFFFAOYSA-N tert-butyl n-(1-hydroxyethyl)carbamate Chemical compound CC(O)NC(=O)OC(C)(C)C FZMZNAWBMQKJRL-UHFFFAOYSA-N 0.000 description 1
QNLCTIFJTPWCDT-UHFFFAOYSA-N tert-butyl n-(2,4,6-trimethylphenyl)sulfonylcarbamate Chemical compound CC1=CC(C)=C(S(=O)(=O)NC(=O)OC(C)(C)C)C(C)=C1 QNLCTIFJTPWCDT-UHFFFAOYSA-N 0.000 description 1
QKSQWQOAUQFORH-UHFFFAOYSA-N tert-butyl n-[(2-methylpropan-2-yl)oxycarbonylimino]carbamate Chemical compound CC(C)(C)OC(=O)N=NC(=O)OC(C)(C)C QKSQWQOAUQFORH-UHFFFAOYSA-N 0.000 description 1
PDJALHZSIRSFBO-UHFFFAOYSA-N tert-butyl n-[2-[2-methyl-5-nitro-6-(1,2,4,5-tetrahydro-3-benzazepin-3-yl)pyrimidin-4-yl]oxyethyl]carbamate Chemical compound CC1=NC(OCCNC(=O)OC(C)(C)C)=C([N+]([O-])=O)C(N2CCC3=CC=CC=C3CC2)=N1 PDJALHZSIRSFBO-UHFFFAOYSA-N 0.000 description 1
OIPJYRGCJUGRNL-UHFFFAOYSA-N tert-butyl n-[5-cyano-2-methyl-6-oxo-4-(1,2,4,5-tetrahydro-3-benzazepin-3-yl)pyrimidin-1-yl]-n-propan-2-ylcarbamate Chemical compound O=C1N(N(C(=O)OC(C)(C)C)C(C)C)C(C)=NC(N2CCC3=CC=CC=C3CC2)=C1C#N OIPJYRGCJUGRNL-UHFFFAOYSA-N 0.000 description 1
RHTNWWCBZRYVAK-UHFFFAOYSA-N tert-butyl n-[[5-cyano-2-methyl-6-oxo-4-(1,2,4,5-tetrahydro-3-benzazepin-3-yl)pyrimidin-1-yl]amino]carbamate Chemical compound O=C1N(NNC(=O)OC(C)(C)C)C(C)=NC(N2CCC3=CC=CC=C3CC2)=C1C#N RHTNWWCBZRYVAK-UHFFFAOYSA-N 0.000 description 1
BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
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GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
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Classifications

- 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
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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
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Obesity (AREA)
Emergency Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Plural Heterocyclic Compounds (AREA)
Other In-Based Heterocyclic Compounds (AREA)

HR20000520A 1999-08-06 2000-08-02 1,2,4,5-TETRADYDRO-BENZO/d/AZEPINES HRP20000520A2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
EP99115557		1999-08-06

Publications (1)

Publication Number	Publication Date
HRP20000520A2 true HRP20000520A2 (en)	2001-06-30

Family

ID=8238742

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HR20000520A HRP20000520A2 (en)	1999-08-06	2000-08-02	1,2,4,5-TETRADYDRO-BENZO/d/AZEPINES

Country Status (27)

Country	Link
US (1)	US6218385B1 (id)
JP (1)	JP3260350B2 (id)
KR (1)	KR100390116B1 (id)
CN (1)	CN1146455C (id)
AR (1)	AR025035A1 (id)
AT (1)	ATE254614T1 (id)
AU (1)	AU774485B2 (id)
BR (1)	BR0003375A (id)
CA (1)	CA2314798A1 (id)
CO (1)	CO5180625A1 (id)
DE (1)	DE60006618T2 (id)
ES (1)	ES2209728T3 (id)
HR (1)	HRP20000520A2 (id)
HU (1)	HUP0003112A3 (id)
ID (1)	ID26743A (id)
IL (1)	IL137688A0 (id)
MA (1)	MA26748A1 (id)
NO (1)	NO20003966L (id)
NZ (1)	NZ506096A (id)
PE (1)	PE20010467A1 (id)
PL (1)	PL341890A1 (id)
RU (1)	RU2240317C2 (id)
SG (1)	SG93251A1 (id)
TR (1)	TR200002298A3 (id)
UY (1)	UY26276A1 (id)
YU (1)	YU49700A (id)
ZA (1)	ZA200003927B (id)

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2000
- 2000-07-27 ES ES00116091T patent/ES2209728T3/es not_active Expired - Lifetime
- 2000-07-27 AT AT00116091T patent/ATE254614T1/de not_active IP Right Cessation
- 2000-07-27 DE DE60006618T patent/DE60006618T2/de not_active Expired - Fee Related
- 2000-08-01 US US09/630,702 patent/US6218385B1/en not_active Expired - Fee Related
- 2000-08-01 NZ NZ506096A patent/NZ506096A/xx unknown
- 2000-08-01 MA MA26033A patent/MA26748A1/fr unknown
- 2000-08-01 CA CA002314798A patent/CA2314798A1/en not_active Abandoned
- 2000-08-02 ID IDP20000655A patent/ID26743A/id unknown
- 2000-08-02 HR HR20000520A patent/HRP20000520A2/hr not_active Application Discontinuation
- 2000-08-02 PE PE2000000768A patent/PE20010467A1/es not_active Application Discontinuation
- 2000-08-02 ZA ZA200003927A patent/ZA200003927B/xx unknown
- 2000-08-02 SG SG200004344A patent/SG93251A1/en unknown
- 2000-08-02 AU AU48979/00A patent/AU774485B2/en not_active Ceased
- 2000-08-03 IL IL13768800A patent/IL137688A0/xx unknown
- 2000-08-03 CO CO00058410A patent/CO5180625A1/es not_active Application Discontinuation
- 2000-08-04 JP JP2000236848A patent/JP3260350B2/ja not_active Expired - Fee Related
- 2000-08-04 KR KR10-2000-0045324A patent/KR100390116B1/ko not_active IP Right Cessation
- 2000-08-04 AR ARP000104022A patent/AR025035A1/es not_active Application Discontinuation
- 2000-08-04 RU RU2000120522/04A patent/RU2240317C2/ru not_active IP Right Cessation
- 2000-08-04 NO NO20003966A patent/NO20003966L/no not_active Application Discontinuation
- 2000-08-04 UY UY26276A patent/UY26276A1/es not_active Application Discontinuation
- 2000-08-04 CN CNB001225235A patent/CN1146455C/zh not_active Expired - Fee Related
- 2000-08-04 TR TR2000/02298A patent/TR200002298A3/tr unknown
- 2000-08-04 HU HU0003112A patent/HUP0003112A3/hu unknown
- 2000-08-07 PL PL00341890A patent/PL341890A1/xx unknown
- 2000-08-07 BR BR0003375-8A patent/BR0003375A/pt not_active Application Discontinuation
- 2000-08-07 YU YU49700A patent/YU49700A/sh unknown

Also Published As

Publication number	Publication date
CA2314798A1 (en)	2001-02-06
JP3260350B2 (ja)	2002-02-25
NO20003966D0 (no)	2000-08-04
NO20003966L (no)	2001-02-07
DE60006618D1 (de)	2003-12-24
US6218385B1 (en)	2001-04-17
RU2240317C2 (ru)	2004-11-20
JP2001089472A (ja)	2001-04-03
ES2209728T3 (es)	2004-07-01
HU0003112D0 (en)	2000-10-28
TR200002298A2 (tr)	2001-03-21
TR200002298A3 (tr)	2001-03-21
AU774485B2 (en)	2004-07-01
IL137688A0 (en)	2001-10-31
DE60006618T2 (de)	2004-09-23
KR20010082510A (ko)	2001-08-30
HUP0003112A2 (hu)	2002-11-28
PL341890A1 (en)	2001-02-12
UY26276A1 (es)	2000-10-31
ZA200003927B (en)	2001-02-06
ATE254614T1 (de)	2003-12-15
KR100390116B1 (ko)	2003-07-04
BR0003375A (pt)	2001-03-13
CN1283623A (zh)	2001-02-14
ID26743A (id)	2001-02-08
HUP0003112A3 (en)	2003-07-28
CN1146455C (zh)	2004-04-21
NZ506096A (en)	2002-08-28
MA26748A1 (fr)	2004-12-20
CO5180625A1 (es)	2002-07-30
AU4897900A (en)	2001-02-08
SG93251A1 (en)	2002-12-17
YU49700A (sh)	2003-04-30
AR025035A1 (es)	2002-11-06
PE20010467A1 (es)	2001-04-17

Legal Events

Date	Code	Title
2001-06-30	A1OB	Publication of a patent application
2001-12-05	AIPI	Request for the grant of a patent on the basis of a substantive examination of a patent application
2004-09-30	ODBC	Application rejected

Publication	Publication Date	Title
HRP20000520A2 (en)	2001-06-30	1,2,4,5-TETRADYDRO-BENZO/d/AZEPINES
EP1074549B1 (en)	2003-11-19	Tetrahydro-benzo(d)azepines and their use as antagonists at metabotropic glutamate receptors
JP3398152B2 (ja)	2003-04-21	１ｎ−アルキル−ｎ−アリールピリミジンアミンおよびその誘導体
US6107301A (en)	2000-08-22	1N-alkyl-N-arylpyrimidinamines and derivatives thereof
ES2313110T3 (es)	2009-03-01	Compuestos de cetolactama y su utilizacion.
CA2689989A1 (en)	2008-12-11	Heterocyclic compounds and uses thereof
EP1646389A1 (en)	2006-04-19	Pyrimidine-2,4-dione derivatives as gonadotropin-releasing hormone receptor antagonists
JPH0597851A (ja)	1993-04-20	窒素含有６員環複素環を結合させるアンギオテンシンｉｉ拮抗薬
JPH05140154A (ja)	1993-06-08	置換チオフエン又はフランを組みこんだアンギオテンシンｉｉ拮抗薬
CA2296014A1 (en)	1999-01-14	Aryl-and arylamino-substituted heterocycles as corticotropin releasing hormone antagonists
KR20140103996A (ko)	2014-08-27	Lrrk2 조절제로서 아미노피리미딘 유도체
ES2340941T3 (es)	2010-06-11	Compuestos de 4-piperazinil-pirimidina adecuados para tretar trastornos que responden a modulacion del receptor d 3 de dopamina.
EP1644342A1 (en)	2006-04-12	Gonadotropin-releasing hormone receptor antagonists and methods relating thereto
MXPA00007661A (en)	2002-07-25	Tetrahydro-benzo(d)azepines and their use as antagonists at metabotropic glutamate receptors
CZ20002831A3 (cs)	2001-03-14	1.2.4.5-Tetrahydrobenzo/d/azepinové deriváty, způsob jejich přípravy a jejich použití
TW200303316A (en)	2003-09-01	Substituted indolizine-like compounds and methods of use