LT3231B - Methylpiperazinoazepine derivatives, preparation and use tereof - Google Patents
Methylpiperazinoazepine derivatives, preparation and use tereof Download PDFInfo
- Publication number
- LT3231B LT3231B LTIP378A LTIP378A LT3231B LT 3231 B LT3231 B LT 3231B LT IP378 A LTIP378 A LT IP378A LT IP378 A LTIP378 A LT IP378A LT 3231 B LT3231 B LT 3231B
- Authority
- LT
- Lithuania
- Prior art keywords
- benzo
- methylpiperazin
- pyrido
- diazepine
- formula
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 6
- LNAMXLRLQJUYFU-UHFFFAOYSA-N 3-methyl-2-piperazin-1-yl-1h-azepine Chemical class N1C=CC=CC(C)=C1N1CCNCC1 LNAMXLRLQJUYFU-UHFFFAOYSA-N 0.000 title abstract 2
- 150000003839 salts Chemical class 0.000 claims abstract description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 89
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 69
- 150000001875 compounds Chemical class 0.000 claims description 40
- 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 38
- 238000000034 method Methods 0.000 claims description 32
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims description 31
- 229910052757 nitrogen Inorganic materials 0.000 claims description 27
- GUJAGMICFDYKNR-UHFFFAOYSA-N 1,4-benzodiazepine Chemical compound N1C=CN=CC2=CC=CC=C12 GUJAGMICFDYKNR-UHFFFAOYSA-N 0.000 claims description 20
- -1 11-trifluoromethylcarbonyl-5- (4-methylpiperazin-1-yl) -1H-pyrido (2,3-b) benzo-1,5-diazepine Chemical compound 0.000 claims description 17
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 8
- ZVAPWJGRRUHKGP-UHFFFAOYSA-N 1h-1,5-benzodiazepine Chemical compound N1C=CC=NC2=CC=CC=C12 ZVAPWJGRRUHKGP-UHFFFAOYSA-N 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical group [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 5
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 229910052711 selenium Inorganic materials 0.000 claims description 5
- VZSGNQQCKWYXBD-WLHGVMLRSA-N C(\C=C\C(=O)O)(=O)O.O1C=CC=NC2=C1C=CC=C2 Chemical compound C(\C=C\C(=O)O)(=O)O.O1C=CC=NC2=C1C=CC=C2 VZSGNQQCKWYXBD-WLHGVMLRSA-N 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- KYISUKFCUZOQQR-WLHGVMLRSA-N (e)-but-2-enedioic acid;6-(4-methylpiperazin-1-yl)pyrido[2,3-b][1,4]benzoxazepine Chemical compound OC(=O)\C=C\C(O)=O.C1CN(C)CCN1C1=NC2=CC=CN=C2OC2=CC=CC=C12 KYISUKFCUZOQQR-WLHGVMLRSA-N 0.000 claims description 3
- HROSFJSGFLYTRU-BTJKTKAUSA-N (z)-but-2-enedioic acid;5-(4-methylpiperazin-1-yl)pyrido[2,3-b][1,5]benzoxazepine Chemical compound OC(=O)\C=C/C(O)=O.C1CN(C)CCN1C1=NC2=CC=CC=C2OC2=NC=CC=C12 HROSFJSGFLYTRU-BTJKTKAUSA-N 0.000 claims description 3
- QPPOMEOQNLTFRU-UHFFFAOYSA-N 1,4-thiazepine Chemical compound S1C=CC=NC=C1 QPPOMEOQNLTFRU-UHFFFAOYSA-N 0.000 claims description 3
- ZESOGRVNADKEGU-UHFFFAOYSA-N 11-(4-methylpiperazin-1-yl)benzo[b][1,5]benzoselenazepine Chemical compound C1CN(C)CCN1[SeH]1C2=CC=CC=C2N=CC2=CC=CC=C21 ZESOGRVNADKEGU-UHFFFAOYSA-N 0.000 claims description 3
- YIWJZRDFRBCBID-UHFFFAOYSA-N 5-(4-methylpiperazin-1-yl)-11h-pyrido[4,3-b][1,5]benzodiazepine Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2NC2=CC=NC=C12 YIWJZRDFRBCBID-UHFFFAOYSA-N 0.000 claims description 3
- QWVMUCNKNQTBRW-UHFFFAOYSA-N 6-(4-methylpiperazin-1-yl)pyrido[2,3-b][1,4]benzothiazepine Chemical compound C1CN(C)CCN1C1=NC2=CC=CN=C2SC2=CC=CC=C12 QWVMUCNKNQTBRW-UHFFFAOYSA-N 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
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- PHXKMRYWZITVNA-WLHGVMLRSA-N C(\C=C\C(=O)O)(=O)O.O1C=CN=CC2=C1C=CC=C2 Chemical compound C(\C=C\C(=O)O)(=O)O.O1C=CN=CC2=C1C=CC=C2 PHXKMRYWZITVNA-WLHGVMLRSA-N 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
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- 150000001860 citric acid derivatives Chemical class 0.000 claims description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 claims description 2
- 150000003840 hydrochlorides Chemical class 0.000 claims description 2
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- 229910052760 oxygen Inorganic materials 0.000 claims description 2
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- 235000021317 phosphate Nutrition 0.000 claims description 2
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- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims description 2
- 239000005711 Benzoic acid Substances 0.000 claims 1
- DLGYNVMUCSTYDQ-UHFFFAOYSA-N azane;pyridine Chemical compound N.C1=CC=NC=C1 DLGYNVMUCSTYDQ-UHFFFAOYSA-N 0.000 claims 1
- 150000001538 azepines Chemical class 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 claims 1
- 239000000932 sedative agent Substances 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
- 238000002844 melting Methods 0.000 description 39
- 230000008018 melting Effects 0.000 description 39
- 239000000203 mixture Substances 0.000 description 32
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
- 239000000047 product Substances 0.000 description 28
- 239000000243 solution Substances 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
- 238000003786 synthesis reaction Methods 0.000 description 23
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- 239000002244 precipitate Substances 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
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- 239000002904 solvent Substances 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- DXZDEAJXVCLRLE-UHFFFAOYSA-N azepin-2-one Chemical class O=C1C=CC=CC=N1 DXZDEAJXVCLRLE-UHFFFAOYSA-N 0.000 description 9
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
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- 238000012360 testing method Methods 0.000 description 8
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 7
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- 238000009835 boiling Methods 0.000 description 7
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
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- FTMBGAIUQQPJDQ-UHFFFAOYSA-N 5h-pyrido[2,3-b][1,4]benzothiazepin-6-one Chemical compound O=C1NC2=CC=CN=C2SC2=CC=CC=C12 FTMBGAIUQQPJDQ-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- 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
-
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D517/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having selenium, tellurium, or halogen atoms as ring hetero atoms
- C07D517/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having selenium, tellurium, or halogen atoms as ring hetero atoms in which the condensed system contains two hetero rings
- C07D517/04—Ortho-condensed systems
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- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurosurgery (AREA)
- General Health & Medical Sciences (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Neurology (AREA)
- Public Health (AREA)
- Psychiatry (AREA)
- Anesthesiology (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE9000914A BE1004596A4 (fr) | 1990-09-26 | 1990-09-26 | Derives de methylpiperazinoazepine, leur preparation et leur utilisation. |
| HK98106195.3A HK1006970B (en) | 1991-10-10 | Methylpiperazinoazepine derivatives, their preparation and use | |
| CA002120229A CA2120229C (fr) | 1990-09-26 | 1991-10-10 | Derives de methylpiperazinoazepine, leur preparation et leur utilisation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| LTIP378A LTIP378A (en) | 1994-09-25 |
| LT3231B true LT3231B (en) | 1995-04-25 |
Family
ID=27159764
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LTIP378A LT3231B (en) | 1990-09-26 | 1993-03-03 | Methylpiperazinoazepine derivatives, preparation and use tereof |
Country Status (13)
| Country | Link |
|---|---|
| EP (1) | EP0607129B1 (et) |
| AT (1) | ATE126799T1 (et) |
| BE (1) | BE1004596A4 (et) |
| CA (1) | CA2120229C (et) |
| DE (1) | DE69112432T2 (et) |
| DK (1) | DK0607129T3 (et) |
| EE (1) | EE02942B1 (et) |
| ES (1) | ES2080336T3 (et) |
| GR (1) | GR3017951T3 (et) |
| LT (1) | LT3231B (et) |
| LV (1) | LV10098B (et) |
| RU (1) | RU2111966C1 (et) |
| WO (1) | WO1993007143A1 (et) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5700445A (en) * | 1994-12-12 | 1997-12-23 | Allelix Biopharmaceuticals, Inc. | N-methyl piperazine compounds having dopamine receptor affinity |
| US5561127A (en) * | 1994-12-19 | 1996-10-01 | Allelix Biopharmaceuticals, Inc. | Muscarinic receptor ligands |
| FR2850654A1 (fr) * | 2003-02-03 | 2004-08-06 | Servier Lab | Nouveaux derives d'azepines tricycliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| ES2324713T3 (es) | 2003-12-22 | 2009-08-13 | Acadia Pharmaceuticals Inc. | Analogos de diaril(a,d)ciclohepteno amino-sustituidos como agonistas muscarinicos y metodos de tratamiento de trastornos neuropsiquiatricos. |
| CN1913900B (zh) * | 2003-12-22 | 2010-11-24 | 阿卡蒂亚药品公司 | 作为毒蕈碱激动剂的氨基取代的二芳基[a，d]环庚烯类似物及神经精神疾病的治疗方法 |
| CN102807574B (zh) * | 2011-05-30 | 2015-09-02 | 长春吉大天元化学技术股份有限公司 | 新型吡啶并硫氮七元环衍生物作为抗肿瘤药物、及其制备方法和应用 |
| CN107382907A (zh) * | 2017-06-21 | 2017-11-24 | 温州医科大学 | 一种11‑甲基二苯并[b,f][1,4]硒吖庚因化合物及制备方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4163785A (en) | 1977-04-07 | 1979-08-07 | Hexachimie | Benzothiazepine compounds and compositions |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7403657A (et) * | 1973-03-23 | 1974-09-25 | ||
| US3872122A (en) * | 1973-04-16 | 1975-03-18 | Bristol Myers Co | 11 H-Pyrimido{8 4,5-b{9 {8 1,4{9 benzodiazepines |
| IT7851496A0 (it) * | 1977-10-31 | 1978-10-13 | Sandoz Ag | Menti pirazinobenzossazepine loro preparazione e loro impiego quali medica |
| CH643263A5 (de) * | 1979-05-11 | 1984-05-30 | Sandoz Ag | Benzodiazepine, ihre herstellung und verwendung. |
| GB8819059D0 (en) * | 1988-08-11 | 1988-09-14 | Lilly Industries Ltd | Benzodiazepine compounds & their use as pharmaceuticals |
| US4940704A (en) | 1989-08-16 | 1990-07-10 | Hoechst-Roussel Pharmaceutical Inc. | Pyrido[3,4-b][1,4]benzoxazepines |
-
1990
- 1990-09-26 BE BE9000914A patent/BE1004596A4/fr not_active IP Right Cessation
-
1991
- 1991-10-10 EP EP91916897A patent/EP0607129B1/fr not_active Expired - Lifetime
- 1991-10-10 CA CA002120229A patent/CA2120229C/fr not_active Expired - Fee Related
- 1991-10-10 ES ES91916897T patent/ES2080336T3/es not_active Expired - Lifetime
- 1991-10-10 DE DE69112432T patent/DE69112432T2/de not_active Expired - Fee Related
- 1991-10-10 RU RU94021365A patent/RU2111966C1/ru not_active IP Right Cessation
- 1991-10-10 DK DK91916897.1T patent/DK0607129T3/da active
- 1991-10-10 AT AT91916897T patent/ATE126799T1/de not_active IP Right Cessation
- 1991-10-10 WO PCT/BE1991/000073 patent/WO1993007143A1/fr not_active Ceased
-
1992
- 1992-12-23 LV LVP-92-398A patent/LV10098B/lv unknown
-
1993
- 1993-03-03 LT LTIP378A patent/LT3231B/lt not_active IP Right Cessation
-
1994
- 1994-10-14 EE EE9400260A patent/EE02942B1/et not_active IP Right Cessation
-
1995
- 1995-11-01 GR GR950403060T patent/GR3017951T3/el unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4163785A (en) | 1977-04-07 | 1979-08-07 | Hexachimie | Benzothiazepine compounds and compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| HK1006970A1 (en) | 1999-03-26 |
| EE02942B1 (et) | 1996-10-15 |
| RU2111966C1 (ru) | 1998-05-27 |
| LV10098B (en) | 1994-10-20 |
| EP0607129A1 (fr) | 1994-07-27 |
| CA2120229A1 (fr) | 1993-04-15 |
| ES2080336T3 (es) | 1996-02-01 |
| CA2120229C (fr) | 2002-04-09 |
| LV10098A (lv) | 1994-05-10 |
| BE1004596A4 (fr) | 1992-12-22 |
| DE69112432D1 (de) | 1995-09-28 |
| ATE126799T1 (de) | 1995-09-15 |
| LTIP378A (en) | 1994-09-25 |
| EP0607129B1 (fr) | 1995-08-23 |
| DE69112432T2 (de) | 1996-02-01 |
| WO1993007143A1 (fr) | 1993-04-15 |
| DK0607129T3 (da) | 1995-12-18 |
| GR3017951T3 (en) | 1996-02-29 |
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Legal Events
| Date | Code | Title | Description |
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| TK9A | Rectifications: patents |
Free format text: 1. METILPIPERAZINAZEPINO DARINYS, KURIO BENDRA FORMULE I: I,KURIOJE:X YRA DEGUONIES ATOMAS, SIEROS ATOMAS, SELENO ATOMAS ARBA NH AR NR3 GRUPE, KURIOJE R3 YRA -C , -C GRUPE, ARBA NESAKOTA AR SAKOTA NUO 1 IKI 4 ANGLIES ATOMU TURINTI ALKILO GRUPE;R1 YRA VANDENILIO ATOMAS, HALOGENO ATOMAS ARBA SAKOTA AR NESAKOTA NUO 1 IKI 4 ANGLIES ATOMU TURINTI ALKILO GRUPE;R2 YRA VANDENILIO ATOMAS, HALOGENO ATOMAS ARBA SAKOTA AR NESAKOTA NUO 1 IKI 4 ANGLIES ATOMU TURINTI ALKILO GRUPE; IR N1 YRA BENZENO ZIEDAS IR N2 PIRIDINO ZIEDAS ARBA ATVIRKSCIAI, SU |
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| TK9A | Rectifications: patents |
Free format text: C07D 241/00, C07D 241/02, C07D 295/00, C07D 295/02, C07D 295/32, 19960616, |
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| PC9A | Transfer of patents |
Owner name: UNIVERSITE DE LIEGE, BE Effective date: 20030326 |
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| MM9A | Lapsed patents |
Effective date: 20040303 |