JP2001516717A - 選択的５−ＨＴ１Ａアンタゴニストおよび選択的ｈ５−ＨＴ１Ｂアンタゴニストまたは部分的アゴニストの組み合わせ - Google Patents
選択的５−ＨＴ１Ａアンタゴニストおよび選択的ｈ５−ＨＴ１Ｂアンタゴニストまたは部分的アゴニストの組み合わせInfo
- Publication number
- JP2001516717A JP2001516717A JP2000511498A JP2000511498A JP2001516717A JP 2001516717 A JP2001516717 A JP 2001516717A JP 2000511498 A JP2000511498 A JP 2000511498A JP 2000511498 A JP2000511498 A JP 2000511498A JP 2001516717 A JP2001516717 A JP 2001516717A
- Authority
- JP
- Japan
- Prior art keywords
- methylpiperazin
- compound
- dihydro
- benzopyran
- tetrahydro
- Prior art date
- 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.)
- Pending
Links
- 239000005557 antagonist Substances 0.000 title claims abstract description 24
- 239000004031 partial agonist Substances 0.000 title claims abstract description 12
- 102100022738 5-hydroxytryptamine receptor 1A Human genes 0.000 title 1
- 101710138638 5-hydroxytryptamine receptor 1A Proteins 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 144
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 43
- 239000001257 hydrogen Substances 0.000 claims abstract description 30
- 238000000034 method Methods 0.000 claims abstract description 30
- 150000003839 salts Chemical class 0.000 claims abstract description 22
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 20
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 19
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 13
- 239000003727 serotonin 1A antagonist Substances 0.000 claims abstract description 13
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 12
- 239000012458 free base Substances 0.000 claims abstract description 11
- 150000002367 halogens Chemical class 0.000 claims abstract description 11
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims abstract description 10
- 239000012453 solvate Substances 0.000 claims abstract description 10
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims abstract description 8
- 208000027534 Emotional disease Diseases 0.000 claims abstract description 7
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims abstract description 7
- 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 claims abstract description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims abstract description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims abstract description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 4
- 238000004519 manufacturing process Methods 0.000 claims abstract 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 69
- -1 4-ethylpiperazin-1-yl Chemical group 0.000 claims description 44
- 239000002585 base Substances 0.000 claims description 36
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 16
- 150000002431 hydrogen Chemical class 0.000 claims description 14
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 12
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 12
- 229910052794 bromium Inorganic materials 0.000 claims description 12
- 238000011282 treatment Methods 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 6
- 230000001225 therapeutic effect Effects 0.000 claims description 5
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 4
- XCSBGPAPGUIEFO-OAQYLSRUSA-N n-[(2r)-5-methoxy-8-(4-methylpiperazin-1-yl)-1,2,3,4-tetrahydronaphthalen-2-yl]-4-morpholin-4-ylbenzamide Chemical compound C([C@H](CC=12)NC(=O)C=3C=CC(=CC=3)N3CCOCC3)CC=1C(OC)=CC=C2N1CCN(C)CC1 XCSBGPAPGUIEFO-OAQYLSRUSA-N 0.000 claims description 4
- HWSWMVFTXFBDRW-JOCHJYFZSA-N n-[(2r)-8-(4-methylpiperazin-1-yl)-1,2,3,4-tetrahydronaphthalen-2-yl]-4-morpholin-4-ylbenzamide Chemical compound C1CN(C)CCN1C1=CC=CC2=C1C[C@H](NC(=O)C=1C=CC(=CC=1)N1CCOCC1)CC2 HWSWMVFTXFBDRW-JOCHJYFZSA-N 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- GGWPSJWVARDUIR-UHFFFAOYSA-N 8-methoxy-5-(4-methylpiperazin-1-yl)-n-(4-morpholin-4-ylphenyl)-3,4-dihydro-2h-chromene-3-carboxamide Chemical compound C1=2CC(C(=O)NC=3C=CC(=CC=3)N3CCOCC3)COC=2C(OC)=CC=C1N1CCN(C)CC1 GGWPSJWVARDUIR-UHFFFAOYSA-N 0.000 claims description 3
- JSPVFUIDFJHLNO-UHFFFAOYSA-N C(CCC)NC1OC2=C(CC1)C=CC=C2F Chemical compound C(CCC)NC1OC2=C(CC1)C=CC=C2F JSPVFUIDFJHLNO-UHFFFAOYSA-N 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- WZMSJJIAEOODBC-JOCHJYFZSA-N n-[(2r)-5-methoxy-8-(4-methylpiperazin-1-yl)-1,2,3,4-tetrahydronaphthalen-2-yl]-4-(morpholine-4-carbonyl)benzamide Chemical compound C([C@H](CC=12)NC(=O)C=3C=CC(=CC=3)C(=O)N3CCOCC3)CC=1C(OC)=CC=C2N1CCN(C)CC1 WZMSJJIAEOODBC-JOCHJYFZSA-N 0.000 claims description 3
- IHDRUIHIJWCTIY-JOCHJYFZSA-N n-[(2r)-5-methyl-8-(4-methylpiperazin-1-yl)-1,2,3,4-tetrahydronaphthalen-2-yl]-4-morpholin-4-ylbenzamide Chemical compound C1CN(C)CCN1C1=CC=C(C)C2=C1C[C@H](NC(=O)C=1C=CC(=CC=1)N1CCOCC1)CC2 IHDRUIHIJWCTIY-JOCHJYFZSA-N 0.000 claims description 3
- VAAMBBBNNWFJHZ-FQEVSTJZSA-N n-[(3s)-5-(4-methylpiperazin-1-yl)-3,4-dihydro-2h-chromen-3-yl]-4-morpholin-4-ylbenzamide Chemical compound C1CN(C)CCN1C1=CC=CC2=C1C[C@H](NC(=O)C=1C=CC(=CC=1)N1CCOCC1)CO2 VAAMBBBNNWFJHZ-FQEVSTJZSA-N 0.000 claims description 3
- 239000004000 serotonin 1B antagonist Substances 0.000 claims description 3
- GLCNLSFPYIMZJK-HXUWFJFHSA-N (2r)-5-methoxy-8-(4-methylpiperazin-1-yl)-n-(4-morpholin-4-ylphenyl)-1,2,3,4-tetrahydronaphthalene-2-carboxamide Chemical compound C([C@H](CC=12)C(=O)NC=3C=CC(=CC=3)N3CCOCC3)CC=1C(OC)=CC=C2N1CCN(C)CC1 GLCNLSFPYIMZJK-HXUWFJFHSA-N 0.000 claims description 2
- JMQUFKWBATWTAM-HXUWFJFHSA-N (2r)-5-methoxy-8-(4-methylpiperazin-1-yl)-n-[2-(morpholine-4-carbonyl)phenyl]-1,2,3,4-tetrahydronaphthalene-2-carboxamide Chemical compound C([C@H](CC=12)C(=O)NC=3C(=CC=CC=3)C(=O)N3CCOCC3)CC=1C(OC)=CC=C2N1CCN(C)CC1 JMQUFKWBATWTAM-HXUWFJFHSA-N 0.000 claims description 2
- GLCNLSFPYIMZJK-FQEVSTJZSA-N (2s)-5-methoxy-8-(4-methylpiperazin-1-yl)-n-(4-morpholin-4-ylphenyl)-1,2,3,4-tetrahydronaphthalene-2-carboxamide Chemical compound C([C@@H](CC=12)C(=O)NC=3C=CC(=CC=3)N3CCOCC3)CC=1C(OC)=CC=C2N1CCN(C)CC1 GLCNLSFPYIMZJK-FQEVSTJZSA-N 0.000 claims description 2
- AOSCUPVQGZCMHA-GFCCVEGCSA-N (3r)-3-[cyclobutyl(propan-2-yl)amino]-8-fluoro-3,4-dihydro-2h-chromene-5-carboxamide Chemical compound CC(C)N([C@@H]1CC2=C(C(N)=O)C=CC(F)=C2OC1)C1CCC1 AOSCUPVQGZCMHA-GFCCVEGCSA-N 0.000 claims description 2
- IAFNMDAKUNVLSN-GFCCVEGCSA-N (3r)-3-[cyclobutyl(propyl)amino]-8-fluoro-3,4-dihydro-2h-chromene-5-carboxamide Chemical compound CCCN([C@@H]1CC2=C(C(N)=O)C=CC(F)=C2OC1)C1CCC1 IAFNMDAKUNVLSN-GFCCVEGCSA-N 0.000 claims description 2
- 239000002671 adjuvant Substances 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- OXZHFWAHGKDGDI-LJQANCHMSA-N n-[(2r)-5-bromo-8-piperazin-1-yl-1,2,3,4-tetrahydronaphthalen-2-yl]-4-morpholin-4-ylbenzamide Chemical compound C([C@H](CC=12)NC(=O)C=3C=CC(=CC=3)N3CCOCC3)CC=1C(Br)=CC=C2N1CCNCC1 OXZHFWAHGKDGDI-LJQANCHMSA-N 0.000 claims description 2
- BEEWOAIWRLZBGZ-HSZRJFAPSA-N n-[(2r)-5-ethyl-8-(4-methylpiperazin-1-yl)-1,2,3,4-tetrahydronaphthalen-2-yl]-4-morpholin-4-ylbenzamide Chemical compound C([C@H](CC=12)NC(=O)C=3C=CC(=CC=3)N3CCOCC3)CC=1C(CC)=CC=C2N1CCN(C)CC1 BEEWOAIWRLZBGZ-HSZRJFAPSA-N 0.000 claims description 2
- SBJHEBVVUMAPPB-UHFFFAOYSA-N C1(CCC1)N(C1CCC1)C1OC2=C(CC1)C=CC=C2F Chemical compound C1(CCC1)N(C1CCC1)C1OC2=C(CC1)C=CC=C2F SBJHEBVVUMAPPB-UHFFFAOYSA-N 0.000 claims 1
- 208000020401 Depressive disease Diseases 0.000 claims 1
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 abstract description 6
- 230000036506 anxiety Effects 0.000 abstract description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 166
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 150
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 145
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 123
- 239000002904 solvent Substances 0.000 description 109
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 102
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 97
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 78
- 238000006243 chemical reaction Methods 0.000 description 76
- 239000000243 solution Substances 0.000 description 69
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 66
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 61
- 238000002451 electron ionisation mass spectrometry Methods 0.000 description 60
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 58
- 238000002360 preparation method Methods 0.000 description 58
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 57
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- 239000003480 eluent Substances 0.000 description 48
- 239000000203 mixture Substances 0.000 description 48
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 44
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- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 44
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- 239000000741 silica gel Substances 0.000 description 33
- 229910002027 silica gel Inorganic materials 0.000 description 33
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 31
- 239000012074 organic phase Substances 0.000 description 30
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- 235000019198 oils Nutrition 0.000 description 23
- 235000011054 acetic acid Nutrition 0.000 description 22
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 22
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- 229910052763 palladium Inorganic materials 0.000 description 21
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- 239000000908 ammonium hydroxide Substances 0.000 description 19
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- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 15
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- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- DUUGKQCEGZLZNO-UHFFFAOYSA-N 5-hydroxyindoleacetic acid Chemical compound C1=C(O)C=C2C(CC(=O)O)=CNC2=C1 DUUGKQCEGZLZNO-UHFFFAOYSA-N 0.000 description 10
- 239000003153 chemical reaction reagent Substances 0.000 description 10
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- 229910000104 sodium hydride Inorganic materials 0.000 description 9
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- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 8
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 7
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 7
- QZRGKCOWNLSUDK-UHFFFAOYSA-N Iodochlorine Chemical compound ICl QZRGKCOWNLSUDK-UHFFFAOYSA-N 0.000 description 7
- 239000013543 active substance Substances 0.000 description 7
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 7
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- 238000001816 cooling Methods 0.000 description 7
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- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
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Classifications
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- A—HUMAN NECESSITIES
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
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- 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
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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- 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
- A61P25/22—Anxiolytics
-
- 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
- A61P25/24—Antidepressants
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE9703374-0 | 1997-09-18 | ||
| SE9703374A SE9703374D0 (sv) | 1997-09-18 | 1997-09-18 | A new combination |
| PCT/SE1998/001600 WO1999013876A1 (en) | 1997-09-18 | 1998-09-09 | A COMBINATION OF A SELECTIVE 5-HT1A ANTAGONIST AND A SELECTIVE h5-HT1B ANTAGONIST OR PARTIAL AGONIST |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2001516717A true JP2001516717A (ja) | 2001-10-02 |
| JP2001516717A5 JP2001516717A5 (https=) | 2006-01-05 |
Family
ID=20408294
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000511498A Pending JP2001516717A (ja) | 1997-09-18 | 1998-09-09 | 選択的５−ＨＴ１Ａアンタゴニストおよび選択的ｈ５−ＨＴ１Ｂアンタゴニストまたは部分的アゴニストの組み合わせ |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US6159972A (https=) |
| EP (1) | EP1021183B1 (https=) |
| JP (1) | JP2001516717A (https=) |
| KR (1) | KR20010024075A (https=) |
| CN (1) | CN1182847C (https=) |
| AR (1) | AR015447A1 (https=) |
| AT (1) | ATE261728T1 (https=) |
| AU (1) | AU752718B2 (https=) |
| BR (1) | BR9812234A (https=) |
| CA (1) | CA2302383A1 (https=) |
| DE (1) | DE69822490T2 (https=) |
| DK (1) | DK1021183T3 (https=) |
| EE (1) | EE04142B1 (https=) |
| ES (1) | ES2216307T3 (https=) |
| HU (1) | HUP0100401A3 (https=) |
| IL (1) | IL134774A0 (https=) |
| IS (1) | IS5408A (https=) |
| MY (1) | MY116281A (https=) |
| NO (1) | NO20001398L (https=) |
| NZ (1) | NZ503174A (https=) |
| PL (1) | PL339370A1 (https=) |
| PT (1) | PT1021183E (https=) |
| RU (1) | RU2215528C2 (https=) |
| SE (1) | SE9703374D0 (https=) |
| SK (1) | SK2842000A3 (https=) |
| TR (1) | TR200000734T2 (https=) |
| TW (1) | TW568786B (https=) |
| WO (1) | WO1999013876A1 (https=) |
| ZA (1) | ZA987810B (https=) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE9601110D0 (sv) | 1996-03-22 | 1996-03-22 | Astra Ab | Substituted 1,2,3,4-tetrahydronaphthalene derivatives |
| SE9703375D0 (sv) * | 1997-09-18 | 1997-09-18 | Astra Ab | A new combination |
| WO2002066454A1 (fr) * | 2001-02-21 | 2002-08-29 | Sankyo Company, Limited | Derives de chromene |
| ATE424825T1 (de) * | 2001-07-20 | 2009-03-15 | Psychogenics Inc | Behandlung von hyperaktivitätsstörungen und aufmerksamkeitsdefiziten |
| US20050165025A1 (en) * | 2004-01-22 | 2005-07-28 | Recordati Ireland Ltd. | Combination therapy with 5HT 1A and 5HT 1B-receptor antagonists |
| USD969016S1 (en) | 2021-06-28 | 2022-11-08 | Koninklijke Asscher Diamant Maatschappij B.V. | Rose oval diamond article |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA90673B (en) * | 1989-02-02 | 1990-10-31 | Yamanouchi Pharma Co Ltd | Tetrahydrobenzimidazole derivatives |
| PT533268E (pt) * | 1991-09-18 | 2002-02-28 | Glaxo Group Ltd | Derivados de benzanilida como antagonistas de 5-ht1d |
| GB9410512D0 (en) * | 1994-05-25 | 1994-07-13 | Smithkline Beecham Plc | Novel treatment |
| SE9501567D0 (sv) * | 1995-04-27 | 1995-04-27 | Astra Ab | A new combination |
| FI961247A0 (fi) * | 1996-03-18 | 1996-03-18 | Finnish Peroxides Ab Oy | Foerfarande foer loesning av uppsvaellningsproblem i en avfalls vattenreningsanordning foer kontroll av traodartiga bakterier |
| SE9601110D0 (sv) * | 1996-03-22 | 1996-03-22 | Astra Ab | Substituted 1,2,3,4-tetrahydronaphthalene derivatives |
-
1997
- 1997-09-18 SE SE9703374A patent/SE9703374D0/xx unknown
-
1998
- 1998-08-27 ZA ZA987810A patent/ZA987810B/xx unknown
- 1998-08-29 TW TW087114345A patent/TW568786B/zh not_active IP Right Cessation
- 1998-09-09 US US09/171,581 patent/US6159972A/en not_active Expired - Fee Related
- 1998-09-09 CN CNB988112493A patent/CN1182847C/zh not_active Expired - Fee Related
- 1998-09-09 ES ES98944374T patent/ES2216307T3/es not_active Expired - Lifetime
- 1998-09-09 AT AT98944374T patent/ATE261728T1/de not_active IP Right Cessation
- 1998-09-09 PT PT98944374T patent/PT1021183E/pt unknown
- 1998-09-09 RU RU2000109558/14A patent/RU2215528C2/ru not_active IP Right Cessation
- 1998-09-09 NZ NZ503174A patent/NZ503174A/en unknown
- 1998-09-09 BR BR9812234-7A patent/BR9812234A/pt not_active IP Right Cessation
- 1998-09-09 EE EEP200000143A patent/EE04142B1/xx not_active IP Right Cessation
- 1998-09-09 HU HU0100401A patent/HUP0100401A3/hu unknown
- 1998-09-09 CA CA002302383A patent/CA2302383A1/en not_active Abandoned
- 1998-09-09 KR KR1020007002821A patent/KR20010024075A/ko not_active Ceased
- 1998-09-09 SK SK284-2000A patent/SK2842000A3/sk unknown
- 1998-09-09 JP JP2000511498A patent/JP2001516717A/ja active Pending
- 1998-09-09 DE DE69822490T patent/DE69822490T2/de not_active Expired - Fee Related
- 1998-09-09 PL PL98339370A patent/PL339370A1/xx unknown
- 1998-09-09 EP EP98944374A patent/EP1021183B1/en not_active Expired - Lifetime
- 1998-09-09 AU AU91929/98A patent/AU752718B2/en not_active Ceased
- 1998-09-09 TR TR2000/00734T patent/TR200000734T2/xx unknown
- 1998-09-09 WO PCT/SE1998/001600 patent/WO1999013876A1/en not_active Ceased
- 1998-09-09 IL IL13477498A patent/IL134774A0/xx unknown
- 1998-09-09 DK DK98944374T patent/DK1021183T3/da active
- 1998-09-16 MY MYPI98004226A patent/MY116281A/en unknown
- 1998-09-17 AR ARP980104633A patent/AR015447A1/es unknown
-
2000
- 2000-03-15 IS IS5408A patent/IS5408A/is unknown
- 2000-03-17 NO NO20001398A patent/NO20001398L/no not_active Application Discontinuation
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