JP3219541B2 - チエノベンゾジアゼピン化合物及びその製法並びにそれを含有する医薬組成物 - Google Patents
チエノベンゾジアゼピン化合物及びその製法並びにそれを含有する医薬組成物Info
- Publication number
- JP3219541B2 JP3219541B2 JP12642993A JP12642993A JP3219541B2 JP 3219541 B2 JP3219541 B2 JP 3219541B2 JP 12642993 A JP12642993 A JP 12642993A JP 12642993 A JP12642993 A JP 12642993A JP 3219541 B2 JP3219541 B2 JP 3219541B2
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- alkyl
- compounds
- compound
- same
- 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.)
- Expired - Fee Related
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 43
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 7
- 238000000034 method Methods 0.000 title description 4
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- 239000001257 hydrogen Substances 0.000 claims abstract description 9
- 239000003085 diluting agent Substances 0.000 claims description 5
- 230000002152 alkylating effect Effects 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract description 7
- 125000000304 alkynyl group Chemical group 0.000 abstract description 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract description 3
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 abstract description 3
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 abstract description 2
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- -1 4-pentenyl Chemical group 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 8
- 239000004480 active ingredient Substances 0.000 description 7
- 150000002367 halogens Chemical class 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 229920002472 Starch Polymers 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 229910052736 halogen Inorganic materials 0.000 description 6
- 235000019698 starch Nutrition 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 102000005962 receptors Human genes 0.000 description 5
- 108020003175 receptors Proteins 0.000 description 5
- 239000008107 starch Substances 0.000 description 5
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 208000019901 Anxiety disease Diseases 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 210000003169 central nervous system Anatomy 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 229930195725 Mannitol Natural products 0.000 description 2
- 208000026139 Memory disease Diseases 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 208000028017 Psychotic disease Diseases 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 229940100198 alkylating agent Drugs 0.000 description 2
- 239000002168 alkylating agent Substances 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 230000036506 anxiety Effects 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 238000010255 intramuscular injection Methods 0.000 description 2
- 239000007927 intramuscular injection Substances 0.000 description 2
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 239000000594 mannitol Substances 0.000 description 2
- 235000010355 mannitol Nutrition 0.000 description 2
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000000159 protein binding assay Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 102220240796 rs553605556 Human genes 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 201000000980 schizophrenia Diseases 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000013268 sustained release Methods 0.000 description 2
- 239000012730 sustained-release form Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 239000003981 vehicle Substances 0.000 description 2
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 1
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- UWYVPFMHMJIBHE-OWOJBTEDSA-N (e)-2-hydroxybut-2-enedioic acid Chemical compound OC(=O)\C=C(\O)C(O)=O UWYVPFMHMJIBHE-OWOJBTEDSA-N 0.000 description 1
- DGKCGLWUGYQUHU-UHFFFAOYSA-N 10-(cyclopropylmethyl)-2-methyl-4-(4-methylpiperazin-1-yl)thieno[2,3-b][1,5]benzodiazepine Chemical compound C1CN(C)CCN1C(C=1C=C(C)SC=11)=NC2=CC=CC=C2N1CC1CC1 DGKCGLWUGYQUHU-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
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- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P25/20—Hypnotics; Sedatives
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A—HUMAN NECESSITIES
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- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- Neurology (AREA)
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- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Addiction (AREA)
- Anesthesiology (AREA)
- Otolaryngology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB929211379A GB9211379D0 (en) | 1992-05-29 | 1992-05-29 | Pharmaceutical compounds |
| GB9211379:4 | 1993-04-30 | ||
| GB9309025:6 | 1993-04-30 | ||
| GB939309025A GB9309025D0 (en) | 1993-04-30 | 1993-04-30 | Pharmaceutical compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0687862A JPH0687862A (ja) | 1994-03-29 |
| JP3219541B2 true JP3219541B2 (ja) | 2001-10-15 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12642993A Expired - Fee Related JP3219541B2 (ja) | 1992-05-29 | 1993-05-28 | チエノベンゾジアゼピン化合物及びその製法並びにそれを含有する医薬組成物 |
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Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US5457101A (en) * | 1994-06-03 | 1995-10-10 | Eli Lilly And Company | Thieno[1,5]benzoidiazepine use |
| US5574028A (en) * | 1994-10-31 | 1996-11-12 | Eli Lilly And Company | Method for treating anxiety |
| CR5278A (es) * | 1995-03-24 | 1996-07-04 | Lilly Co Eli | Formulacion oral de 2-metil-tieno-benzodiacepina |
| EG24221A (en) * | 1995-03-24 | 2008-11-10 | Lilly Co Eli | Process for preparing olanzapine |
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| US5891461A (en) * | 1995-09-14 | 1999-04-06 | Cygnus, Inc. | Transdermal administration of olanzapine |
| AU725556B2 (en) * | 1996-03-25 | 2000-10-12 | Eli Lilly And Company | Method for treating pain |
| UA44838C2 (uk) * | 1996-03-25 | 2002-03-15 | Елі Ліллі Енд Компані | Спосіб лікування мігрені |
| CN1219878A (zh) * | 1996-03-25 | 1999-06-16 | 伊莱利利公司 | 治疗疼痛的方法 |
| PL194074B1 (pl) | 1996-09-23 | 2007-04-30 | Lilly Co Eli | Polimorf Dihydrat D olanzapiny i preparat farmaceutyczny zawierający Dihydrat D olanzapiny |
| ZA978515B (en) * | 1996-09-23 | 1999-03-23 | Lilly Co Eli | Intermediates and process for preparing olanzapine |
| ID21762A (id) * | 1996-09-24 | 1999-07-22 | Lilly Co Eli | Formulasi partikel bersaput |
| RU2185383C1 (ru) * | 2001-05-22 | 2002-07-20 | Институт молекулярной генетики РАН | ВЫСОКОМЕЧЕННЫЙ ТРИТИЕМ 2-МЕТИЛ-4-(4-МЕТИЛ-1-ПИПЕРАЗИНИЛ)-10Н-ТИЕНО[2,3-b][1,5]БЕНЗОДИАЗЕПИН |
| CN108640996A (zh) | 2012-08-21 | 2018-10-12 | 詹森药业有限公司 | 帕潘立酮的抗体及其用途 |
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| CA2882563C (en) | 2012-08-21 | 2022-11-29 | Eric Hryhorenko | Antibodies to risperidone haptens and use thereof |
| PL3462173T3 (pl) | 2012-08-21 | 2021-08-16 | Janssen Pharmaceutica Nv | Przeciwciała przeciwko rysperydonowi i ich zastosowanie |
| JP6131415B2 (ja) | 2012-08-21 | 2017-05-24 | ヤンセン ファーマシューティカ エヌ．ベー． | イムノアッセイに使用するためのクエチアピンのハプテン |
| JP2015529199A (ja) | 2012-08-21 | 2015-10-05 | オルソ−クリニカル ダイアグノスティクス，インコーポレイティド | パリペリドンハプテンに対する抗体及びその使用 |
| PT3663317T (pt) | 2012-08-21 | 2023-01-23 | Janssen Pharmaceutica Nv | Anticorpos para haptenos de quetiapina e sua utilização |
| PT3415516T (pt) | 2012-08-21 | 2022-01-28 | Janssen Pharmaceutica Nv | Haptenos de risperidona e paliperidona |
| US9494608B2 (en) | 2012-08-21 | 2016-11-15 | Janssen Pharmaceutica Nv | Antibodies to olanzapine and use thereof |
| AU2013305907B2 (en) | 2012-08-21 | 2018-01-18 | Saladax Biomedical Inc. | Antibodies to quetiapine and use thereof |
| ES2733963T3 (es) | 2012-08-21 | 2019-12-03 | Janssen Pharmaceutica Nv | Anticuerpos contra haptenos de olanzapina y uso de los mismos |
| CN104736567B (zh) | 2012-08-21 | 2019-09-03 | 詹森药业有限公司 | 阿立哌唑半抗原的抗体及其用途 |
| PL3321254T3 (pl) | 2012-08-21 | 2021-01-11 | Janssen Pharmaceutica Nv | Hapteny arypiprazolu i ich zastosowanie w testach immunologicznych |
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| ES2739383T3 (es) | 2012-08-21 | 2020-01-30 | Janssen Pharmaceutica Nv | Haptenos de paliperidona |
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| CH569731A5 (cg-RX-API-DMAC7.html) * | 1972-04-04 | 1975-11-28 | Wander Ag Dr A | |
| US3962248A (en) * | 1972-04-04 | 1976-06-08 | Sandoz, Inc. | Process for making 11-piperazino-diazepines, oxazepines, thiazepines and azepines |
| SU629879A3 (ru) * | 1974-11-26 | 1978-10-25 | Лилли Индастриз Лимитед, (Фирма) | Способ получени тиено(1,5) бензодиазепинов или их солей |
| US4061752A (en) * | 1975-08-06 | 1977-12-06 | Sandoz Ltd. | 6-Piperazino-11-methylene-dibenzazepines[b,e] |
| DE2641378A1 (de) * | 1975-09-24 | 1977-04-07 | Sandoz Ag | Neue organische verbindungen, ihre verwendung und herstellung |
| CH624682A5 (cg-RX-API-DMAC7.html) * | 1976-11-10 | 1981-08-14 | Sandoz Ag | |
| US4761411A (en) * | 1983-05-18 | 1988-08-02 | Hoechst-Roussel Pharmaceuticals Inc. | Dihydrobenzopyrrolobenzodiazepines useful for treating pyschoses |
| GB9009229D0 (en) * | 1990-04-25 | 1990-06-20 | Lilly Industries Ltd | Pharmaceutical compounds |
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1993
- 1993-05-26 TW TW082104161A patent/TW268005B/zh active
- 1993-05-26 EP EP93304102A patent/EP0582368B1/en not_active Expired - Lifetime
- 1993-05-26 ES ES93304102T patent/ES2153373T3/es not_active Expired - Lifetime
- 1993-05-26 CA CA002097016A patent/CA2097016A1/en not_active Abandoned
- 1993-05-26 AT AT93304102T patent/ATE198891T1/de not_active IP Right Cessation
- 1993-05-26 PT PT93304102T patent/PT582368E/pt unknown
- 1993-05-26 AU AU39807/93A patent/AU668159B2/en not_active Ceased
- 1993-05-26 DK DK93304102T patent/DK0582368T3/da active
- 1993-05-26 NO NO931917A patent/NO305125B1/no not_active IP Right Cessation
- 1993-05-26 DE DE69329887T patent/DE69329887T2/de not_active Expired - Fee Related
- 1993-05-26 NZ NZ247703A patent/NZ247703A/en unknown
- 1993-05-27 MX MX9303124A patent/MX9303124A/es not_active IP Right Cessation
- 1993-05-28 IL IL10582793A patent/IL105827A/xx not_active IP Right Cessation
- 1993-05-28 JP JP12642993A patent/JP3219541B2/ja not_active Expired - Fee Related
- 1993-05-28 CZ CZ931024A patent/CZ282783B6/cs not_active IP Right Cessation
- 1993-05-28 FI FI932445A patent/FI101538B/fi active
- 1993-05-28 RU RU93005057A patent/RU2125574C1/ru active
- 1993-05-28 CN CN93108212A patent/CN1043994C/zh not_active Expired - Fee Related
- 1993-05-28 HU HU9301579A patent/HU218278B/hu not_active IP Right Cessation
- 1993-05-28 MY MYPI93001036A patent/MY109943A/en unknown
-
2001
- 2001-03-15 GR GR20010400431T patent/GR3035587T3/el not_active IP Right Cessation
Non-Patent Citations (1)
| Title |
|---|
| Ｊ．Ｍｅｄ．Ｃｈｅｍ．，Ｖｏｌ．２３（１９８０）Ｐ．８７８−８８４ |
Also Published As
| Publication number | Publication date |
|---|---|
| NO305125B1 (no) | 1999-04-06 |
| DK0582368T3 (da) | 2001-02-05 |
| CZ102493A3 (en) | 1993-12-15 |
| DE69329887T2 (de) | 2001-05-23 |
| FI101538B1 (fi) | 1998-07-15 |
| IL105827A0 (en) | 1993-09-22 |
| EP0582368A1 (en) | 1994-02-09 |
| CN1085903A (zh) | 1994-04-27 |
| AU3980793A (en) | 1993-12-02 |
| HU9301579D0 (en) | 1993-09-28 |
| CN1043994C (zh) | 1999-07-07 |
| NO931917L (no) | 1993-11-30 |
| MY109943A (en) | 1997-10-31 |
| TW268005B (cg-RX-API-DMAC7.html) | 1996-01-11 |
| GR3035587T3 (en) | 2001-06-29 |
| RU2125574C1 (ru) | 1999-01-27 |
| HUT66180A (en) | 1994-09-28 |
| NZ247703A (en) | 1995-07-26 |
| FI932445A0 (fi) | 1993-05-28 |
| HU218278B (en) | 2000-07-28 |
| JPH0687862A (ja) | 1994-03-29 |
| NO931917D0 (no) | 1993-05-26 |
| CA2097016A1 (en) | 1993-11-30 |
| CZ282783B6 (cs) | 1997-10-15 |
| PT582368E (pt) | 2001-05-31 |
| FI101538B (fi) | 1998-07-15 |
| MX9303124A (es) | 1993-11-01 |
| ES2153373T3 (es) | 2001-03-01 |
| IL105827A (en) | 1997-02-18 |
| EP0582368B1 (en) | 2001-01-24 |
| FI932445L (fi) | 1993-11-30 |
| DE69329887D1 (de) | 2001-03-01 |
| ATE198891T1 (de) | 2001-02-15 |
| AU668159B2 (en) | 1996-04-26 |
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