PH27118A - Anticonvulsant compounds - Google Patents

Anticonvulsant compounds Download PDF

Info

Publication number: PH27118A
Authority: PH; Philippines
Prior art keywords: compound; difluoro; pharmaceutically; formula; alpyridine
Prior art date: 1989-04-21

Application number

PH40399A

Other languages

English (en)

Inventor

James Leroy Kelley

Original Assignee

Wellcome Found

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.)

1989-04-21

Filing date

1990-04-19

Publication date

1993-03-16

1990-04-19 Application filed by Wellcome Found filed Critical Wellcome Found

1993-03-16 Publication of PH27118A publication Critical patent/PH27118A/en

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 56
239000001961 anticonvulsive agent Substances 0.000 title description 9
229960003965 antiepileptics Drugs 0.000 title description 7
230000001773 anti-convulsant effect Effects 0.000 title description 6
238000002360 preparation method Methods 0.000 claims abstract description 20
238000000034 method Methods 0.000 claims abstract description 12
239000008194 pharmaceutical composition Chemical class 0.000 claims abstract description 3
238000006243 chemical reaction Methods 0.000 claims description 13
150000003839 salts Chemical class 0.000 claims description 10
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
150000001412 amines Chemical class 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 5
150000002431 hydrogen Chemical class 0.000 claims description 4
PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 claims description 4
GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical compound CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
125000001153 fluoro group Chemical group F* 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 1
206010015037 epilepsy Diseases 0.000 abstract description 6
241000124008 Mammalia Species 0.000 abstract description 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 4
YWBFPKPWMSWWEA-UHFFFAOYSA-O triazolopyrimidine Chemical class BrC1=CC=CC(C=2N=C3N=CN[N+]3=C(NCC=3C=CN=CC=3)C=2)=C1 YWBFPKPWMSWWEA-UHFFFAOYSA-O 0.000 abstract 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 40
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 23
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
BAVYZALUXZFZLV-UHFFFAOYSA-N mono-methylamine Natural products NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 18
239000000243 solution Substances 0.000 description 18
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
239000007787 solid Substances 0.000 description 14
239000000203 mixture Substances 0.000 description 11
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 11
235000019439 ethyl acetate Nutrition 0.000 description 10
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
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125000001309 chloro group Chemical group Cl* 0.000 description 6
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QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 5
239000008213 purified water Substances 0.000 description 5
-1 triazolopyridine Chemical class 0.000 description 5
HLTDBMHJSBSAOM-UHFFFAOYSA-N 2-nitropyridine Chemical compound [O-][N+](=O)C1=CC=CC=N1 HLTDBMHJSBSAOM-UHFFFAOYSA-N 0.000 description 4
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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 4
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 4
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238000005481 NMR spectroscopy Methods 0.000 description 3
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239000002585 base Substances 0.000 description 3
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IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 3
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150000002500 ions Chemical class 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000000843 powder Substances 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
235000010288 sodium nitrite Nutrition 0.000 description 3
239000006188 syrup Substances 0.000 description 3
235000020357 syrup Nutrition 0.000 description 3
238000005160 1H NMR spectroscopy Methods 0.000 description 2
125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
206010010904 Convulsion Diseases 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
208000034308 Grand mal convulsion Diseases 0.000 description 2
241000282412 Homo Species 0.000 description 2
IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
208000000260 Warts Diseases 0.000 description 2
230000002159 abnormal effect Effects 0.000 description 2
150000003927 aminopyridines Chemical class 0.000 description 2
239000003963 antioxidant agent Substances 0.000 description 2
235000006708 antioxidants Nutrition 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
239000000969 carrier Substances 0.000 description 2
208000015114 central nervous system disease Diseases 0.000 description 2
229940110456 cocoa butter Drugs 0.000 description 2
235000019868 cocoa butter Nutrition 0.000 description 2
238000004040 coloring Methods 0.000 description 2
150000004683 dihydrates Chemical class 0.000 description 2
239000012458 free base Substances 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
239000011777 magnesium Substances 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
239000001267 polyvinylpyrrolidone Substances 0.000 description 2
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201000010153 skin papilloma Diseases 0.000 description 2
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FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Chemical compound O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 2
TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
PQCUDKMMPTXMAL-UHFFFAOYSA-N (2,6-difluorophenyl)methanamine Chemical compound NCC1=C(F)C=CC=C1F PQCUDKMMPTXMAL-UHFFFAOYSA-N 0.000 description 1
LRFWYBZWRQWZIM-UHFFFAOYSA-N (2-fluorophenyl)methanamine Chemical compound NCC1=CC=CC=C1F LRFWYBZWRQWZIM-UHFFFAOYSA-N 0.000 description 1
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QEASJVYPHMYPJM-UHFFFAOYSA-N 1,2-dihydrotriazol-5-one Chemical compound OC1=CNN=N1 QEASJVYPHMYPJM-UHFFFAOYSA-N 0.000 description 1
BHKKSKOHRFHHIN-MRVPVSSYSA-N 1-[[2-[(1R)-1-aminoethyl]-4-chlorophenyl]methyl]-2-sulfanylidene-5H-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound N[C@H](C)C1=C(CN2C(NC(C3=C2C=CN3)=O)=S)C=CC(=C1)Cl BHKKSKOHRFHHIN-MRVPVSSYSA-N 0.000 description 1
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235000011150 stannous chloride Nutrition 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
230000008719 thickening Effects 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
OVCXRBARSPBVMC-UHFFFAOYSA-N triazolopyridine Chemical compound C=1N2C(C(C)C)=NN=C2C=CC=1C=1OC=NC=1C1=CC=C(F)C=C1 OVCXRBARSPBVMC-UHFFFAOYSA-N 0.000 description 1
150000008523 triazolopyridines Chemical class 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
239000008215 water for injection Substances 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- 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
- A61P25/08—Antiepileptics; Anticonvulsants

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Life Sciences & Earth Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Pain & Pain Management (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pyridine Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

PH40399A 1989-04-21 1990-04-19 Anticonvulsant compounds PH27118A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB898909136A GB8909136D0 (en)	1989-04-21	1989-04-21	Anticonvulsant pyridines and analogues thereof

Publications (1)

Publication Number	Publication Date
PH27118A true PH27118A (en)	1993-03-16

Family

ID=10655494

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
PH40399A PH27118A (en)	1989-04-21	1990-04-19	Anticonvulsant compounds

Country Status (21)

Country	Link
EP (1)	EP0399653B1 (pt)
JP (1)	JP2865367B2 (pt)
KR (1)	KR0183972B1 (pt)
AT (1)	ATE113046T1 (pt)
CA (1)	CA2015047A1 (pt)
CY (1)	CY2003B1 (pt)
DD (1)	DD293823A5 (pt)
DE (1)	DE69013396T2 (pt)
DK (1)	DK0399653T3 (pt)
ES (1)	ES2062351T3 (pt)
FI (1)	FI93448C (pt)
GB (1)	GB8909136D0 (pt)
HK (1)	HK78397A (pt)
HU (2)	HU206210B (pt)
IE (1)	IE67335B1 (pt)
IL (1)	IL94150A (pt)
LV (1)	LV5780B4 (pt)
NZ (1)	NZ233404A (pt)
PH (1)	PH27118A (pt)
PT (1)	PT93822B (pt)
ZA (1)	ZA903021B (pt)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA2334836A1 (en) *	1998-06-16	1999-12-23	Merck Sharp & Dohme Limited	Triazolo-pyridine derivatives as ligands for gaba receptors

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3929812A (en) *	1974-05-20	1975-12-30	Squibb & Sons Inc	Derivatives of 1H-triazolo {8 4,5-c{9 pyridine-7-carboxylic acids and esters
DE3873812D1 (de) *	1987-04-07	1992-09-24	Ciba Geigy Ag	3h-1,2,3-triazolo(4,5-d)pyrimidine.

1989
- 1989-04-21 GB GB898909136A patent/GB8909136D0/en active Pending
1990
- 1990-04-19 PH PH40399A patent/PH27118A/en unknown
- 1990-04-20 DE DE69013396T patent/DE69013396T2/de not_active Expired - Fee Related
- 1990-04-20 EP EP90304271A patent/EP0399653B1/en not_active Expired - Lifetime
- 1990-04-20 DK DK90304271.1T patent/DK0399653T3/da active
- 1990-04-20 FI FI901981A patent/FI93448C/fi not_active IP Right Cessation
- 1990-04-20 DD DD90339946A patent/DD293823A5/de not_active IP Right Cessation
- 1990-04-20 KR KR1019900005523A patent/KR0183972B1/ko not_active IP Right Cessation
- 1990-04-20 PT PT93822A patent/PT93822B/pt not_active IP Right Cessation
- 1990-04-20 JP JP2105156A patent/JP2865367B2/ja not_active Expired - Lifetime
- 1990-04-20 HU HU902502A patent/HU206210B/hu not_active IP Right Cessation
- 1990-04-20 IL IL9415090A patent/IL94150A/en not_active IP Right Cessation
- 1990-04-20 CA CA002015047A patent/CA2015047A1/en not_active Abandoned
- 1990-04-20 ZA ZA903021A patent/ZA903021B/xx unknown
- 1990-04-20 IE IE140990A patent/IE67335B1/en not_active IP Right Cessation
- 1990-04-20 NZ NZ233404A patent/NZ233404A/en unknown
- 1990-04-20 AT AT90304271T patent/ATE113046T1/de not_active IP Right Cessation
- 1990-04-20 ES ES90304271T patent/ES2062351T3/es not_active Expired - Lifetime
1995
- 1995-05-11 HU HU95P/P00126P patent/HU211137A9/hu unknown
1996
- 1996-07-17 LV LV960252A patent/LV5780B4/xx unknown
1997
- 1997-06-12 HK HK78397A patent/HK78397A/xx not_active IP Right Cessation
1998
- 1998-04-30 CY CY9802003A patent/CY2003B1/xx unknown

Also Published As

Publication number	Publication date
NZ233404A (en)	1992-08-26
AU626409B2 (en)	1992-07-30
IL94150A0 (en)	1991-01-31
HU211137A9 (en)	1995-10-30
ZA903021B (en)	1991-12-24
CY2003B1 (en)	1998-04-30
ATE113046T1 (de)	1994-11-15
FI93448B (fi)	1994-12-30
FI901981A0 (fi)	1990-04-20
JPH02292286A (ja)	1990-12-03
HU206210B (en)	1992-09-28
IL94150A (en)	1994-02-27
HK78397A (en)	1997-06-20
DK0399653T3 (da)	1994-11-14
HU902502D0 (en)	1990-08-28
DE69013396T2 (de)	1995-05-04
JP2865367B2 (ja)	1999-03-08
IE67335B1 (en)	1996-03-20
PT93822B (pt)	1996-09-30
LV5780A4 (lv)	1996-12-20
EP0399653B1 (en)	1994-10-19
EP0399653A1 (en)	1990-11-28
DD293823A5 (de)	1991-09-12
PT93822A (pt)	1990-11-20
LV5780B4 (lv)	1997-04-20
KR0183972B1 (ko)	1999-05-01
HUT53905A (en)	1990-12-28
GB8909136D0 (en)	1989-06-07
KR900016208A (ko)	1990-11-12
FI93448C (fi)	1995-04-10
AU5372290A (en)	1990-10-25
IE901409L (en)	1990-10-21
ES2062351T3 (es)	1994-12-16
CA2015047A1 (en)	1990-10-21
DE69013396D1 (de)	1994-11-24

Publication	Publication Date	Title
AU742941B2 (en)	2002-01-17	Sustained release tablet formulation to treat parkinson disease
AU630251B2 (en)	1992-10-22	Dipyridodiazepines
SK277923B6 (en)	1995-08-09	3-imidazolymethyl-1,2,3,9-tetrahydro-4h-carbazole-4-on derivatives, method of their preparation and pharmaceutical agents containing this agents
IE883900L (en)	1989-07-25	Antibacterial agents
HU208823B (en)	1994-01-28	Process for producing new thiophenecarboxylic acid esters of amino-alcohols, their quaternary derivatives and pharmaceutical compositions comprising them as active ingredient
DD297820A5 (de)	1992-01-23	Substituierte 9h-purine, verfahren zur herstellung derselben und ihre verwendung
KR100201509B1 (ko)	1999-06-15	1-(피리도(3,4-b-1,4-옥사지닐-4일-)-1h-인돌, 이를 위한 중간체, 이의 제조방법 및 이를 포함하는 약제학적 조성물
PH27118A (en)	1993-03-16	Anticonvulsant compounds
US4095027A (en)	1978-06-13	2-Carbalkoxy-2'-aminocarbonyldiphenyl sulfides
FI66611B (fi)	1984-07-31	Foerfarande foer framstaellning av nya terapeutiskt anvaendbara fenyl-kinolizidiner
US5240937A (en)	1993-08-31	Pharmaceutically active triazolopyridine compounds
US6395905B1 (en)	2002-05-28	Tetrahydroindazole derivatives as ligands for GABA-A α 5 receptors
JP3027762B2 (ja)	2000-04-04	抗痙攣性ピラジン
US5958920A (en)	1999-09-28	Aralkyl diazabicycloalkane derivatives for CNS disorders
EP0406719A1 (en)	1991-01-09	4h-indolo(1,2-d)(1,2,4)triazolo (4,3-a)(1,4)benzodiazepines, a process for their preparation and their use as medicaments
US5166209A (en)	1992-11-24	Pharmacologically active compounds
NL8701728A (nl)	1988-02-16	Heterocyclische verbindingen.
US4044014A (en)	1977-08-23	Sulfide compounds
EP0534344A1 (en)	1993-03-31	Substituted 3-amino-2,3,4,5-tetrahydro-1-aryloxy-3-benzazepines, a process for their preparation and their use as modulators of neurotransmitter function
US6656930B2 (en)	2003-12-02	Aralkyl diazabicycloalkane derivatives for CNS disorders
JPH09500912A (ja)	1997-01-28	イミダゾ〔１，５−ａ〕インドール−３−オンのイミダゾリルアルキル誘導体およびそれらの製造法