KR20040091638A - 아자-스피로 화합물 - Google Patents
아자-스피로 화합물 Download PDFInfo
- Publication number
- KR20040091638A KR20040091638A KR10-2004-7012680A KR20047012680A KR20040091638A KR 20040091638 A KR20040091638 A KR 20040091638A KR 20047012680 A KR20047012680 A KR 20047012680A KR 20040091638 A KR20040091638 A KR 20040091638A
- Authority
- KR
- South Korea
- Prior art keywords
- azaspiro
- hydrogen
- alkyl
- amino
- compound
- 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.)
- Ceased
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- 150000008627 azaspiro compounds Chemical class 0.000 title claims abstract description 48
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 38
- 208000002193 Pain Diseases 0.000 claims abstract description 34
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 29
- 125000003368 amide group Chemical group 0.000 claims abstract description 28
- 239000003814 drug Substances 0.000 claims abstract description 24
- 125000000464 thioxo group Chemical group S=* 0.000 claims abstract description 20
- 150000003839 salts Chemical class 0.000 claims abstract description 13
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 11
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 9
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 9
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 8
- 239000000546 pharmaceutical excipient Substances 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims description 59
- 229910052739 hydrogen Inorganic materials 0.000 claims description 59
- -1 hydroxy, formyl Chemical group 0.000 claims description 57
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 34
- 150000002431 hydrogen Chemical class 0.000 claims description 25
- 229910052736 halogen Inorganic materials 0.000 claims description 24
- 150000002367 halogens Chemical class 0.000 claims description 24
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 19
- 125000004429 atom Chemical group 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 15
- 150000002430 hydrocarbons Chemical group 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 125000003282 alkyl amino group Chemical group 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000004414 alkyl thio group Chemical group 0.000 claims description 11
- 229920006395 saturated elastomer Polymers 0.000 claims description 11
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 10
- 230000001684 chronic effect Effects 0.000 claims description 10
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 9
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 9
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 9
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims description 9
- 230000000926 neurological effect Effects 0.000 claims description 9
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 125000004043 oxo group Chemical group O=* 0.000 claims description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 5
- 235000013305 food Nutrition 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
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- QNCQJIYBTSFVTE-UHFFFAOYSA-N C1NC(CC12CCCCCC2)=S.C2NC(CC21CCCC1)=S.C1NC(CC12CCCCC2)=S.C2NCCC21CCCCC1 Chemical compound C1NC(CC12CCCCCC2)=S.C2NC(CC21CCCC1)=S.C1NC(CC12CCCCC2)=S.C2NCCC21CCCCC1 QNCQJIYBTSFVTE-UHFFFAOYSA-N 0.000 claims 3
- 238000012360 testing method Methods 0.000 abstract description 24
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract description 18
- JAWPQJDOQPSNIQ-UHFFFAOYSA-N 2-Azaspiro[4.5]decan-3-one Chemical compound C1NC(=O)CC21CCCCC2 JAWPQJDOQPSNIQ-UHFFFAOYSA-N 0.000 abstract description 14
- RBRHMJWQHKXACY-UHFFFAOYSA-N 2-azaspiro[4.6]undecane-3-thione Chemical compound C1NC(=S)CC21CCCCCC2 RBRHMJWQHKXACY-UHFFFAOYSA-N 0.000 abstract description 8
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- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract 6
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- UGJMXCAKCUNAIE-UHFFFAOYSA-N Gabapentin Chemical compound OC(=O)CC1(CN)CCCCC1 UGJMXCAKCUNAIE-UHFFFAOYSA-N 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
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- SFCOKGCNIPSUQF-UHFFFAOYSA-N 2-azaspiro[4.5]decane Chemical compound C1NCCC21CCCCC2 SFCOKGCNIPSUQF-UHFFFAOYSA-N 0.000 description 7
- VQISVGCZRGIOFD-UHFFFAOYSA-N 2-azaspiro[4.5]decane-3-thione Chemical compound C1NC(=S)CC21CCCCC2 VQISVGCZRGIOFD-UHFFFAOYSA-N 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
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- ZOYWDMBYQNFNDE-UHFFFAOYSA-N 2-azaspiro[4.4]nonane-3-thione Chemical compound C1NC(=S)CC11CCCC1 ZOYWDMBYQNFNDE-UHFFFAOYSA-N 0.000 description 5
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- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000003153 chemical reaction reagent Substances 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
- 239000003480 eluent Substances 0.000 description 3
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- 208000021722 neuropathic pain Diseases 0.000 description 3
- 150000002923 oximes Chemical class 0.000 description 3
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 3
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 2
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
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- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
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- 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 2
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- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 description 1
- 208000019906 panic disease Diseases 0.000 description 1
- 230000001991 pathophysiological effect Effects 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 210000001428 peripheral nervous system Anatomy 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 150000004040 pyrrolidinones Chemical class 0.000 description 1
- 238000011552 rat model Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000009938 salting Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000036280 sedation Effects 0.000 description 1
- 229940125723 sedative agent Drugs 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 210000000278 spinal cord Anatomy 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 235000011044 succinic acid Nutrition 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 231100000816 toxic dose Toxicity 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
- 238000010200 validation analysis Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/54—Spiro-condensed
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D497/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having oxygen and sulfur atoms as the only ring hetero atoms
- C07D497/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having oxygen and sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D497/10—Spiro-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pain & Pain Management (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10210190A DE10210190A1 (de) | 2002-03-07 | 2002-03-07 | Aza-Spiroverbindungen |
| DE10210190.6 | 2002-03-07 | ||
| PCT/EP2003/001986 WO2003074486A1 (de) | 2002-03-07 | 2003-02-27 | Aza-spiroverbindungen zur behandlug von schmerzen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20040091638A true KR20040091638A (ko) | 2004-10-28 |
Family
ID=27771112
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR10-2004-7012680A Ceased KR20040091638A (ko) | 2002-03-07 | 2003-02-27 | 아자-스피로 화합물 |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US20050288351A1 (https=) |
| EP (2) | EP1520854A3 (https=) |
| JP (1) | JP2005526745A (https=) |
| KR (1) | KR20040091638A (https=) |
| CN (1) | CN1324011C (https=) |
| AT (1) | ATE298745T1 (https=) |
| AU (1) | AU2003215603A1 (https=) |
| BR (1) | BR0307922A (https=) |
| CA (1) | CA2477124A1 (https=) |
| DE (2) | DE10210190A1 (https=) |
| ES (1) | ES2242944T3 (https=) |
| MX (1) | MXPA04008669A (https=) |
| NO (1) | NO20044239L (https=) |
| PL (1) | PL372431A1 (https=) |
| PT (1) | PT1485352E (https=) |
| RU (1) | RU2322438C2 (https=) |
| UA (1) | UA78987C2 (https=) |
| WO (1) | WO2003074486A1 (https=) |
| ZA (1) | ZA200406245B (https=) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW201607923A (zh) * | 2014-07-15 | 2016-03-01 | 歌林達有限公司 | 被取代之氮螺環（４．５）癸烷衍生物 |
| CN107216335B (zh) * | 2017-06-29 | 2019-04-30 | 上海药明康德新药开发有限公司 | 一种叔丁基1-(羟甲基)-3-氧杂-9-氮杂螺[5.5]十一烷-9-甲酸基酯制法 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2866734A (en) * | 1956-12-05 | 1958-12-30 | Us Vitamin Corp | 3-pyridylethyl 2, 4-oxazolidinediones and process |
| US3150143A (en) * | 1960-07-19 | 1964-09-22 | Geschicketer Fund For Medical | Therapeutically active nu-substituted azaspiranes |
| US3398151A (en) * | 1966-02-01 | 1968-08-20 | Mead Johnson & Co | Azaspirodecanediones and azaspiroundecanediones |
| US3629276A (en) * | 1969-07-16 | 1971-12-21 | Abbott Lab | 2-amino-5-spiro-substituted-oxazo compounds |
| US4430335A (en) * | 1983-02-09 | 1984-02-07 | Hoechst-Roussel Pharmaceuticals Inc. | Substituted 1-azaspiro[4,5]decanes and their analgesic compositions |
| GB8916447D0 (en) * | 1989-07-19 | 1989-09-06 | Ici Plc | Composition,process and use |
| US5319135A (en) * | 1989-08-25 | 1994-06-07 | Warner-Lambert Company | Process for cyclic amino acid anticonvulsant compounds |
| US5132451A (en) * | 1989-08-25 | 1992-07-21 | Warner-Lambert Company | Process for cyclic amino acid anticonvulsant compounds |
| RU95114363A (ru) * | 1992-11-09 | 1997-03-20 | Дзе Бутс Компани ПЛС. (GB) | Производные азаспиросоединений, способ их получения, фармацевтическая композиция, средства для лечения ожирения, средства для лечения аффективных расстройств |
| US5925672A (en) * | 1996-12-06 | 1999-07-20 | Neurosciences Research Foundation, Inc. | Methods of treating mental diseases, inflammation and pain |
| GB9708484D0 (en) * | 1997-04-25 | 1997-06-18 | Merck Sharp & Dohme | Therapeutic agents |
| DE19732928C2 (de) * | 1997-07-31 | 2000-05-18 | Gruenenthal Gmbh | Verwendung substituierter Imidazolidin-2,4-dion-Verbindungen als Schmerzmittel |
| US5948807A (en) * | 1997-09-03 | 1999-09-07 | Regents Of The University Of Minnesota | Spiroindanamines and Spiroindanimides |
| DE19751062A1 (de) * | 1997-11-18 | 1999-07-08 | Univ Ludwigs Albert | An 4-Stellung substituierte 2-Pyrrolidinon-Derivate zur Verringerung des extrazellulären Glutamat-Spiegels |
| WO1999061424A1 (en) * | 1998-05-26 | 1999-12-02 | Warner-Lambert Company | Conformationally constrained amino acid compounds having affinity for the alpha2delta subunit of a calcium channel |
-
2002
- 2002-03-07 DE DE10210190A patent/DE10210190A1/de not_active Ceased
-
2003
- 2003-02-27 MX MXPA04008669A patent/MXPA04008669A/es not_active Application Discontinuation
- 2003-02-27 WO PCT/EP2003/001986 patent/WO2003074486A1/de not_active Ceased
- 2003-02-27 CA CA002477124A patent/CA2477124A1/en not_active Abandoned
- 2003-02-27 EP EP04029311A patent/EP1520854A3/de not_active Withdrawn
- 2003-02-27 AU AU2003215603A patent/AU2003215603A1/en not_active Abandoned
- 2003-02-27 KR KR10-2004-7012680A patent/KR20040091638A/ko not_active Ceased
- 2003-02-27 ES ES03743342T patent/ES2242944T3/es not_active Expired - Lifetime
- 2003-02-27 UA UA20041008091A patent/UA78987C2/uk unknown
- 2003-02-27 AT AT03743342T patent/ATE298745T1/de not_active IP Right Cessation
- 2003-02-27 EP EP03743342A patent/EP1485352B1/de not_active Expired - Lifetime
- 2003-02-27 JP JP2003572956A patent/JP2005526745A/ja active Pending
- 2003-02-27 CN CNB038054388A patent/CN1324011C/zh not_active Expired - Fee Related
- 2003-02-27 PL PL03372431A patent/PL372431A1/xx not_active Application Discontinuation
- 2003-02-27 PT PT03743342T patent/PT1485352E/pt unknown
- 2003-02-27 RU RU2004129769/04A patent/RU2322438C2/ru not_active IP Right Cessation
- 2003-02-27 BR BR0307922-8A patent/BR0307922A/pt not_active IP Right Cessation
- 2003-02-27 DE DE50300710T patent/DE50300710D1/de not_active Expired - Fee Related
-
2004
- 2004-08-05 ZA ZA200406245A patent/ZA200406245B/xx unknown
- 2004-09-07 US US10/936,134 patent/US20050288351A1/en not_active Abandoned
- 2004-10-06 NO NO20044239A patent/NO20044239L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| EP1485352A1 (de) | 2004-12-15 |
| PT1485352E (pt) | 2005-10-31 |
| DE10210190A1 (de) | 2003-09-25 |
| CN1639122A (zh) | 2005-07-13 |
| EP1520854A2 (de) | 2005-04-06 |
| ES2242944T3 (es) | 2005-11-16 |
| RU2322438C2 (ru) | 2008-04-20 |
| AU2003215603A2 (en) | 2003-09-16 |
| CA2477124A1 (en) | 2003-09-12 |
| DE50300710D1 (de) | 2005-08-04 |
| RU2004129769A (ru) | 2005-07-10 |
| WO2003074486A1 (de) | 2003-09-12 |
| EP1520854A3 (de) | 2007-02-21 |
| NO20044239L (no) | 2004-12-01 |
| EP1485352B1 (de) | 2005-06-29 |
| BR0307922A (pt) | 2004-12-21 |
| JP2005526745A (ja) | 2005-09-08 |
| AU2003215603A1 (en) | 2003-09-16 |
| PL372431A1 (en) | 2005-07-25 |
| US20050288351A1 (en) | 2005-12-29 |
| MXPA04008669A (es) | 2004-12-06 |
| ZA200406245B (en) | 2005-06-13 |
| CN1324011C (zh) | 2007-07-04 |
| ATE298745T1 (de) | 2005-07-15 |
| UA78987C2 (en) | 2007-05-10 |
| HK1080468A1 (zh) | 2006-04-28 |
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| PA0201 | Request for examination |
Patent event code: PA02012R01D Patent event date: 20061207 Comment text: Request for Examination of Application |
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