CA2008571A1 - Pyridazino[4,5-]indolizines - Google Patents

Pyridazino[4,5-]indolizines

Info

Publication number: CA2008571A1
Authority: CA; Canada
Prior art keywords: indolizin; pharmaceutically acceptable; acceptable salt; methylpyridazino; amine
Prior art date: 1990-01-12
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

CA002008571A

Other languages

English (en)

Inventor

Annmarie L. Sabb

Magid A. Abou-Gharbia

Gervais Dionne

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.)

Wyeth LLC

Original Assignee

American Home Products Corp

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.)

1990-01-12

Filing date

1990-01-25

Publication date

1991-07-25

1990-01-12 Priority claimed from US07/464,468 external-priority patent/US4985560A/en

1990-01-25 Application filed by American Home Products Corp filed Critical American Home Products Corp

1990-01-25 Priority to CA002008571A priority Critical patent/CA2008571A1/fr

1991-07-25 Publication of CA2008571A1 publication Critical patent/CA2008571A1/fr

Status Abandoned legal-status Critical Current

Links

PGGGVKAOVPSSFH-UHFFFAOYSA-N pyridazino[4,5-b]indolizine Chemical class C1=CC=CC2=CC3=CN=NC=C3N21 PGGGVKAOVPSSFH-UHFFFAOYSA-N 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 65
150000003839 salts Chemical class 0.000 claims abstract description 63
-1 nitro, amino Chemical group 0.000 claims abstract description 43
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
VDIRWFJGJMAYBX-UHFFFAOYSA-N indolizin-1-amine Chemical compound C1=CC=CC2=C(N)C=CN21 VDIRWFJGJMAYBX-UHFFFAOYSA-N 0.000 claims description 3
BFMWUKBKQUKRII-UHFFFAOYSA-N 4-methyl-n-(3-pyrrolidin-1-ylpropyl)pyridazino[4,5-b]indolizin-1-amine Chemical compound C1=2C=C3C=CC=CN3C=2C(C)=NN=C1NCCCN1CCCC1 BFMWUKBKQUKRII-UHFFFAOYSA-N 0.000 claims description 2
RIDRORLXGPSSCS-UHFFFAOYSA-N 4-methyl-n-[2-(1-methylpyrrol-2-yl)ethyl]pyridazino[4,5-b]indolizin-1-amine Chemical compound C1=2C=C3C=CC=CN3C=2C(C)=NN=C1NCCC1=CC=CN1C RIDRORLXGPSSCS-UHFFFAOYSA-N 0.000 claims description 2
NHXREPNUOGXCCC-UHFFFAOYSA-N 4-methyl-n-[3-(2-methylpiperidin-1-yl)propyl]pyridazino[4,5-b]indolizin-1-amine Chemical compound CC1CCCCN1CCCNC1=NN=C(C)C2=C1C=C1N2C=CC=C1 NHXREPNUOGXCCC-UHFFFAOYSA-N 0.000 claims description 2
SCKPXKBHFUGJLW-UHFFFAOYSA-N 4-methyl-n-[2-(1-methylpyrrolidin-2-yl)ethyl]pyridazino[4,5-b]indolizin-1-amine Chemical compound CN1CCCC1CCNC1=NN=C(C)C2=C1C=C1N2C=CC=C1 SCKPXKBHFUGJLW-UHFFFAOYSA-N 0.000 claims 2
KNALSKZPKCYFBS-UHFFFAOYSA-N 1-n-(1-azabicyclo[2.2.2]octan-3-yl)-2-n-(4-methylpyridazino[4,5-b]indolizin-1-yl)propane-1,2-diamine Chemical compound C1=C2C=CC=CN2C2=C1C(NC(CNC1C3CCN(CC3)C1)C)=NN=C2C KNALSKZPKCYFBS-UHFFFAOYSA-N 0.000 claims 1
ODGCQTPEVZGLKD-UHFFFAOYSA-N 2-(3-imidazol-1-ylpropyl)-4-methyl-1h-pyridazino[4,5-b]indolizine Chemical compound C1C=2C=C3C=CC=CN3C=2C(C)=NN1CCCN1C=CN=C1 ODGCQTPEVZGLKD-UHFFFAOYSA-N 0.000 claims 1
RZKXMMQBMRAKSB-UHFFFAOYSA-N 4-(4-methylpyridazino[4,5-b]indolizin-1-yl)piperazine-1-carbaldehyde Chemical compound C1=2C=C3C=CC=CN3C=2C(C)=NN=C1N1CCN(C=O)CC1 RZKXMMQBMRAKSB-UHFFFAOYSA-N 0.000 claims 1
HCKLZOJBIFREPT-UHFFFAOYSA-N 4-methyl-1-(4-methylpiperazin-1-yl)pyridazino[4,5-b]indolizine Chemical compound C1CN(C)CCN1C1=NN=C(C)C2=C1C=C1N2C=CC=C1 HCKLZOJBIFREPT-UHFFFAOYSA-N 0.000 claims 1
WACPDKAYDLBORN-UHFFFAOYSA-N 4-methyl-n-(2-morpholin-4-ylethyl)pyridazino[4,5-b]indolizin-1-amine Chemical compound C1=2C=C3C=CC=CN3C=2C(C)=NN=C1NCCN1CCOCC1 WACPDKAYDLBORN-UHFFFAOYSA-N 0.000 claims 1
QZSGPUSRNBRKAV-UHFFFAOYSA-N 4-methyl-n-(2-pyridin-2-ylethyl)pyridazino[4,5-b]indolizin-1-amine Chemical compound C1=2C=C3C=CC=CN3C=2C(C)=NN=C1NCCC1=CC=CC=N1 QZSGPUSRNBRKAV-UHFFFAOYSA-N 0.000 claims 1
COWVYRZVHULQPL-UHFFFAOYSA-N 4-methyl-n-(3-morpholin-4-ylpropyl)pyridazino[4,5-b]indolizin-1-amine Chemical compound C1=2C=C3C=CC=CN3C=2C(C)=NN=C1NCCCN1CCOCC1 COWVYRZVHULQPL-UHFFFAOYSA-N 0.000 claims 1
PNUBQFHZMQUXBF-UHFFFAOYSA-N 4-methyl-n-(3-piperidin-1-ylpropyl)pyridazino[4,5-b]indolizin-1-amine Chemical compound C1=2C=C3C=CC=CN3C=2C(C)=NN=C1NCCCN1CCCCC1 PNUBQFHZMQUXBF-UHFFFAOYSA-N 0.000 claims 1
ANGVXCZTDBYPOM-UHFFFAOYSA-N 4-methyl-n-(4-morpholin-4-ylbutyl)pyridazino[4,5-b]indolizin-1-amine Chemical compound C1=2C=C3C=CC=CN3C=2C(C)=NN=C1NCCCCN1CCOCC1 ANGVXCZTDBYPOM-UHFFFAOYSA-N 0.000 claims 1
RKSXEJWFWWIZJD-UHFFFAOYSA-N 4-methyl-n-(4-piperazin-1-ylpentyl)pyridazino[4,5-b]indolizin-1-amine Chemical compound N=1N=C(C)C(N2C=CC=CC2=C2)=C2C=1NCCCC(C)N1CCNCC1 RKSXEJWFWWIZJD-UHFFFAOYSA-N 0.000 claims 1
PAULUECSBFOEJZ-UHFFFAOYSA-N 4-methyl-n-(4-pyrrolidin-1-ylbutyl)pyridazino[4,5-b]indolizin-1-amine Chemical compound C1=2C=C3C=CC=CN3C=2C(C)=NN=C1NCCCCN1CCCC1 PAULUECSBFOEJZ-UHFFFAOYSA-N 0.000 claims 1
XCMCKTKXWWRBOE-UHFFFAOYSA-N 4-methyl-n-[2-(4-pyrimidin-2-ylpiperazin-1-yl)ethyl]pyridazino[4,5-b]indolizin-1-amine Chemical compound C1=2C=C3C=CC=CN3C=2C(C)=NN=C1NCCN(CC1)CCN1C1=NC=CC=N1 XCMCKTKXWWRBOE-UHFFFAOYSA-N 0.000 claims 1
QGNANQVCIKSOKI-UHFFFAOYSA-N 4-methyl-n-[2-(4-pyrimidin-2-ylpiperazin-1-yl)propyl]pyridazino[4,5-b]indolizin-1-amine Chemical compound N=1N=C(C)C(N2C=CC=CC2=C2)=C2C=1NCC(C)N(CC1)CCN1C1=NC=CC=N1 QGNANQVCIKSOKI-UHFFFAOYSA-N 0.000 claims 1
SQQRCGTZJRICKR-UHFFFAOYSA-N 4-methyl-n-[3-(4-methylpiperazin-1-yl)propyl]pyridazino[4,5-b]indolizin-1-amine Chemical compound C1CN(C)CCN1CCCNC1=NN=C(C)C2=C1C=C1N2C=CC=C1 SQQRCGTZJRICKR-UHFFFAOYSA-N 0.000 claims 1
FVBOLURHABGCMU-UHFFFAOYSA-N n',n'-diethyl-n-(4-methylpyridazino[4,5-b]indolizin-1-yl)propane-1,3-diamine Chemical compound C1=C2C=CC=CN2C2=C1C(NCCCN(CC)CC)=NN=C2C FVBOLURHABGCMU-UHFFFAOYSA-N 0.000 claims 1
OXCWHZSNSYHWKN-UHFFFAOYSA-N n',n'-dimethyl-n-(4-methylpyridazino[4,5-b]indolizin-1-yl)butane-1,4-diamine Chemical compound C1=C2C=CC=CN2C2=C1C(NCCCCN(C)C)=NN=C2C OXCWHZSNSYHWKN-UHFFFAOYSA-N 0.000 claims 1
AZOSUPKCAHHMFB-UHFFFAOYSA-N n',n'-dimethyl-n-(4-methylpyridazino[4,5-b]indolizin-1-yl)propane-1,3-diamine Chemical compound C1=C2C=CC=CN2C2=C1C(NCCCN(C)C)=NN=C2C AZOSUPKCAHHMFB-UHFFFAOYSA-N 0.000 claims 1
YMVHTGLTEDRWBT-UHFFFAOYSA-N n-(1-azabicyclo[2.2.2]octan-3-yl)-n'-(4-methylpyridazino[4,5-b]indolizin-1-yl)ethane-1,2-diamine Chemical compound C1=C2C=CC=CN2C2=C1C(NCCNC1C3CCN(CC3)C1)=NN=C2C YMVHTGLTEDRWBT-UHFFFAOYSA-N 0.000 claims 1
NIVHVEYGIAQNGF-UHFFFAOYSA-N n-(4-bicyclo[3.2.1]octanyl)-n'-(4-methylpyridazino[4,5-b]indolizin-1-yl)ethane-1,2-diamine Chemical compound C1=C2C=CC=CN2C2=C1C(NCCNC1C3CCC(C3)CC1)=NN=C2C NIVHVEYGIAQNGF-UHFFFAOYSA-N 0.000 claims 1
GTVJBKKPEDCTTI-UHFFFAOYSA-N n-[4-(3-azabicyclo[3.2.2]nonan-3-yl)butyl]-4-methylpyridazino[4,5-b]indolizin-1-amine Chemical compound C1CC(C2)CCC1CN2CCCCNC1=NN=C(C)C2=C1C=C1N2C=CC=C1 GTVJBKKPEDCTTI-UHFFFAOYSA-N 0.000 claims 1
125000000217 alkyl group Chemical group 0.000 abstract description 24
125000004432 carbon atom Chemical group C* 0.000 abstract description 18
229910052739 hydrogen Inorganic materials 0.000 abstract description 15
239000001257 hydrogen Substances 0.000 abstract description 15
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 13
206010012289 Dementia Diseases 0.000 abstract description 12
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 10
230000001713 cholinergic effect Effects 0.000 abstract description 8
125000003545 alkoxy group Chemical group 0.000 abstract description 6
125000004093 cyano group Chemical group *C#N 0.000 abstract description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract description 4
125000003373 pyrazinyl group Chemical group 0.000 abstract description 4
125000004076 pyridyl group Chemical group 0.000 abstract description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract description 4
125000000714 pyrimidinyl group Chemical group 0.000 abstract description 3
239000000018 receptor agonist Substances 0.000 abstract description 3
229940044601 receptor agonist Drugs 0.000 abstract description 3
125000001424 substituent group Chemical group 0.000 abstract description 3
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 abstract description 2
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 abstract description 2
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 abstract description 2
102000017927 CHRM1 Human genes 0.000 abstract description 2
101150073075 Chrm1 gene Proteins 0.000 abstract description 2
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract description 2
239000005977 Ethylene Substances 0.000 abstract description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 2
125000003670 adamantan-2-yl group Chemical group [H]C1([H])C(C2([H])[H])([H])C([H])([H])C3([H])C([*])([H])C1([H])C([H])([H])C2([H])C3([H])[H] 0.000 abstract description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract description 2
125000004663 dialkyl amino group Chemical group 0.000 abstract description 2
125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 abstract description 2
125000001475 halogen functional group Chemical group 0.000 abstract 3
125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 135
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 43
239000012458 free base Substances 0.000 description 32
238000000034 method Methods 0.000 description 24
238000000921 elemental analysis Methods 0.000 description 22
238000006243 chemical reaction Methods 0.000 description 21
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 19
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
229930000680 A04AD01 - Scopolamine Natural products 0.000 description 14
STECJAGHUSJQJN-GAUPFVANSA-N Hyoscine Natural products C1([C@H](CO)C(=O)OC2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-GAUPFVANSA-N 0.000 description 14
STECJAGHUSJQJN-UHFFFAOYSA-N N-Methyl-scopolamin Natural products C1C(C2C3O2)N(C)C3CC1OC(=O)C(CO)C1=CC=CC=C1 STECJAGHUSJQJN-UHFFFAOYSA-N 0.000 description 14
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229960002646 scopolamine Drugs 0.000 description 14
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LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
239000000741 silica gel Substances 0.000 description 12
229910002027 silica gel Inorganic materials 0.000 description 12
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150000001412 amines Chemical class 0.000 description 10
230000000694 effects Effects 0.000 description 10
239000000047 product Substances 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
239000007787 solid Substances 0.000 description 9
238000012360 testing method Methods 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
WOJQJEHWUZOHSW-UHFFFAOYSA-N 1-chloro-4-methylpyridazino[4,5-b]indolizine Chemical compound C1=C2C=CC=CN2C2=C1C(Cl)=NN=C2C WOJQJEHWUZOHSW-UHFFFAOYSA-N 0.000 description 7
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
235000019439 ethyl acetate Nutrition 0.000 description 7
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238000002474 experimental method Methods 0.000 description 5
125000005843 halogen group Chemical group 0.000 description 5
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IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
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238000000746 purification Methods 0.000 description 5
238000003756 stirring Methods 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
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PNHGJPJOMCXSKN-UHFFFAOYSA-N 2-(1-methylpyrrolidin-2-yl)ethanamine Chemical compound CN1CCCC1CCN PNHGJPJOMCXSKN-UHFFFAOYSA-N 0.000 description 3
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 3
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OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical group CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 3
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PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
235000019270 ammonium chloride Nutrition 0.000 description 3
125000004429 atom Chemical group 0.000 description 3
238000009835 boiling Methods 0.000 description 3
210000002932 cholinergic neuron Anatomy 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
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239000003814 drug Substances 0.000 description 3
208000013403 hyperactivity Diseases 0.000 description 3
KPYKFQNTASVHIG-UHFFFAOYSA-N indolizine Chemical compound C1=CC=CC2=C=C[CH]N21 KPYKFQNTASVHIG-UHFFFAOYSA-N 0.000 description 3
239000000203 mixture Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000012299 nitrogen atmosphere Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
238000002560 therapeutic procedure Methods 0.000 description 3
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
JMUCXULQKPWSTJ-UHFFFAOYSA-N 3-piperidin-1-ylpropan-1-amine Chemical compound NCCCN1CCCCC1 JMUCXULQKPWSTJ-UHFFFAOYSA-N 0.000 description 2
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Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

CA002008571A 1990-01-12 1990-01-25 Pyridazino[4,5-]indolizines Abandoned CA2008571A1 (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA002008571A CA2008571A1 (fr)	1990-01-12	1990-01-25	Pyridazino[4,5-]indolizines

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US07/464,468 US4985560A (en)	1990-01-12	1990-01-12	Pyridazino(4,5-b)indolizines
CA002008571A CA2008571A1 (fr)	1990-01-12	1990-01-25	Pyridazino[4,5-]indolizines

Publications (1)

Publication Number	Publication Date
CA2008571A1 true CA2008571A1 (fr)	1991-07-25

Family

ID=25673906

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002008571A Abandoned CA2008571A1 (fr)	1990-01-12	1990-01-25	Pyridazino[4,5-]indolizines

Country Status (1)

Country	Link
CA (1)	CA2008571A1 (fr)

1990
- 1990-01-25 CA CA002008571A patent/CA2008571A1/fr not_active Abandoned

Legal Events

Date	Code	Title	Description
1993-07-25	FZDE	Discontinued

Publication	Publication Date	Title
US4985560A (en)	1991-01-15	Pyridazino(4,5-b)indolizines
US5958931A (en)	1999-09-28	Phenyl-substituted 5H-thiazolo 3,2-A!pyrimidine derivative glutamate receptor antagonists
US5597826A (en)	1997-01-28	Compositions containing sertraline and a 5-HT1D receptor agonist or antagonist
JP3138540B2 (ja)	2001-02-26	置換シクロプロピルアミノ−１，３，５−トリアジン化合物
JPH08333363A (ja)	1996-12-17	インドール誘導体
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