ES2248840T3 - Antagonistas de vasopresina v1a no peptidilicos. - Google Patents
Antagonistas de vasopresina v1a no peptidilicos.Info
- Publication number
- ES2248840T3 ES2248840T3 ES97907895T ES97907895T ES2248840T3 ES 2248840 T3 ES2248840 T3 ES 2248840T3 ES 97907895 T ES97907895 T ES 97907895T ES 97907895 T ES97907895 T ES 97907895T ES 2248840 T3 ES2248840 T3 ES 2248840T3
- Authority
- ES
- Spain
- Prior art keywords
- alkyl
- amino
- phenyl
- optionally substituted
- alkoxy
- 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 - Lifetime
Links
- 239000005557 antagonist Substances 0.000 title description 29
- -1 azetidin-2-on-1-yl Chemical group 0.000 claims description 514
- 150000001875 compounds Chemical class 0.000 claims description 191
- 125000000217 alkyl group Chemical group 0.000 claims description 104
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 73
- 125000003545 alkoxy group Chemical group 0.000 claims description 55
- 239000002253 acid Substances 0.000 claims description 51
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 51
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 44
- 239000001257 hydrogen Substances 0.000 claims description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims description 37
- 125000001424 substituent group Chemical group 0.000 claims description 36
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 35
- 229910052799 carbon Inorganic materials 0.000 claims description 24
- 239000003814 drug Substances 0.000 claims description 24
- 229910052736 halogen Inorganic materials 0.000 claims description 24
- 150000002367 halogens Chemical class 0.000 claims description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
- 208000035475 disorder Diseases 0.000 claims description 22
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
- 229940079593 drug Drugs 0.000 claims description 21
- 125000003386 piperidinyl group Chemical group 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 125000002947 alkylene group Chemical group 0.000 claims description 17
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 14
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 12
- 125000001624 naphthyl group Chemical group 0.000 claims description 11
- 125000004193 piperazinyl group Chemical group 0.000 claims description 11
- 230000027455 binding Effects 0.000 claims description 10
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 10
- 241000282414 Homo sapiens Species 0.000 claims description 9
- 125000002541 furyl group Chemical group 0.000 claims description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
- 125000004076 pyridyl group Chemical group 0.000 claims description 9
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 9
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
- 241000124008 Mammalia Species 0.000 claims description 7
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 7
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims description 7
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 6
- 125000002883 imidazolyl group Chemical group 0.000 claims description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 208000019901 Anxiety disease Diseases 0.000 claims description 5
- 230000036506 anxiety Effects 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 5
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 5
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 claims description 4
- 239000012453 solvate Substances 0.000 claims description 4
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 239000003981 vehicle Substances 0.000 claims description 4
- WKEUBDFSRNJNQL-UHFFFAOYSA-N 1,2-dihydroxypentan-3-one Chemical compound CCC(=O)C(O)CO WKEUBDFSRNJNQL-UHFFFAOYSA-N 0.000 claims description 3
- SEYLPRWNVFCVRQ-UHFFFAOYSA-N 3,4-dihydroxybutan-2-one Chemical compound CC(=O)C(O)CO SEYLPRWNVFCVRQ-UHFFFAOYSA-N 0.000 claims description 3
- 206010019280 Heart failures Diseases 0.000 claims description 3
- 125000003368 amide group Chemical group 0.000 claims description 3
- 239000003146 anticoagulant agent Substances 0.000 claims description 3
- 229960004676 antithrombotic agent Drugs 0.000 claims description 3
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 125000001589 carboacyl group Chemical group 0.000 claims description 3
- 150000003857 carboxamides Chemical class 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 3
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 3
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 3
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 3
- 125000002757 morpholinyl group Chemical group 0.000 claims description 3
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 3
- 125000002971 oxazolyl group Chemical group 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- 125000005493 quinolyl group Chemical group 0.000 claims description 3
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 3
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 3
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- 150000004677 hydrates Chemical class 0.000 claims description 2
- 150000002596 lactones Chemical class 0.000 claims description 2
- 125000005544 phthalimido group Chemical group 0.000 claims description 2
- 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 description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 10
- 125000001475 halogen functional group Chemical group 0.000 claims 9
- 150000002431 hydrogen Chemical group 0.000 claims 5
- 239000002671 adjuvant Substances 0.000 claims 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 1
- 125000004001 thioalkyl group Chemical group 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 55
- 102000004136 Vasopressin Receptors Human genes 0.000 abstract description 14
- 108090000643 Vasopressin Receptors Proteins 0.000 abstract description 14
- 230000008485 antagonism Effects 0.000 abstract description 3
- RZRRJTZLVKZGRN-UHFFFAOYSA-N 2-(2-oxoazetidin-1-yl)acetic acid Chemical class OC(=O)CN1CCC1=O RZRRJTZLVKZGRN-UHFFFAOYSA-N 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 124
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 81
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- 239000000203 mixture Substances 0.000 description 73
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- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 71
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 65
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- 230000002829 reductive effect Effects 0.000 description 58
- 239000000243 solution Substances 0.000 description 54
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 44
- KBZOIRJILGZLEJ-LGYYRGKSSA-N argipressin Chemical compound C([C@H]1C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CSSC[C@@H](C(N[C@@H](CC=2C=CC(O)=CC=2)C(=O)N1)=O)N)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCN=C(N)N)C(=O)NCC(N)=O)C1=CC=CC=C1 KBZOIRJILGZLEJ-LGYYRGKSSA-N 0.000 description 41
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 40
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 32
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 30
- 229940007550 benzyl acetate Drugs 0.000 description 30
- 238000012360 testing method Methods 0.000 description 30
- 108010004977 Vasopressins Proteins 0.000 description 29
- 210000004027 cell Anatomy 0.000 description 29
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
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- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 28
- GXBMIBRIOWHPDT-UHFFFAOYSA-N Vasopressin Natural products N1C(=O)C(CC=2C=C(O)C=CC=2)NC(=O)C(N)CSSCC(C(=O)N2C(CCC2)C(=O)NC(CCCN=C(N)N)C(=O)NCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(CCC(N)=O)NC(=O)C1CC1=CC=CC=C1 GXBMIBRIOWHPDT-UHFFFAOYSA-N 0.000 description 27
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- 238000006243 chemical reaction Methods 0.000 description 24
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P9/00—Drugs for disorders of the cardiovascular system
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
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- Pain & Pain Management (AREA)
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- Urology & Nephrology (AREA)
- Psychiatry (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Bidet-Like Cleaning Device And Other Flush Toilet Accessories (AREA)
- Ultra Sonic Daignosis Equipment (AREA)
Applications Claiming Priority (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1218896P | 1996-02-23 | 1996-02-23 | |
| US1214996P | 1996-02-23 | 1996-02-23 | |
| US1221596P | 1996-02-23 | 1996-02-23 | |
| US12215P | 1996-02-23 | ||
| US12149P | 1996-02-23 | ||
| US12188P | 1996-02-23 | ||
| GBGB9605044.8A GB9605044D0 (en) | 1996-03-09 | 1996-03-09 | Method and non-peptidyl agents for modulation of the vasopressin v1a receptor |
| GBGB9605046.3A GB9605046D0 (en) | 1996-03-09 | 1996-03-09 | Method for antagonism of the tachykinin receptor with non-peptide agents |
| GB9605044 | 1996-03-09 | ||
| GB9605045 | 1996-03-09 | ||
| GB9605046 | 1996-03-09 | ||
| GBGB9605045.5A GB9605045D0 (en) | 1996-03-09 | 1996-03-09 | Method and non-peptidyl agents for modulation of the oxytocin receptor |
| PCT/US1997/003039 WO1997030707A1 (en) | 1996-02-23 | 1997-02-20 | NON-PEPTIDYL VASOPRESSIN V1a ANTAGONISTS |
Publications (1)
| Publication Number | Publication Date |
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| ES2248840T3 true ES2248840T3 (es) | 2006-03-16 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES97907895T Expired - Lifetime ES2248840T3 (es) | 1996-02-23 | 1997-02-20 | Antagonistas de vasopresina v1a no peptidilicos. |
Country Status (10)
| Country | Link |
|---|---|
| US (3) | US6204260B1 (enExample) |
| EP (1) | EP0939632B1 (enExample) |
| JP (1) | JP4212112B2 (enExample) |
| AT (1) | ATE305781T1 (enExample) |
| AU (1) | AU1977997A (enExample) |
| CA (1) | CA2246753C (enExample) |
| DE (1) | DE69734321T2 (enExample) |
| DK (1) | DK0939632T3 (enExample) |
| ES (1) | ES2248840T3 (enExample) |
| WO (1) | WO1997030707A1 (enExample) |
Families Citing this family (27)
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| US6426342B2 (en) * | 1999-08-16 | 2002-07-30 | Revaax Pharmaceuticals, Llc | Use of β-lactamase inhibitors as neuroprotectants |
| US6489319B2 (en) * | 1999-08-16 | 2002-12-03 | Revaax Pharmaceuticals, Llc | Neurotherapeutic use of carboxypeptidase inhibitors |
| CN1382047A (zh) * | 1999-08-16 | 2002-11-27 | 雷瓦尔克斯药品有限公司 | 神经病治疗组合物和方法 |
| BR0015299A (pt) | 1999-11-04 | 2003-04-15 | Johnson & Johnson | Benzotiazepinas substituìdas não-peptìdicas como antagonistas de vasopressina |
| DK1406893T3 (da) | 2001-06-15 | 2007-08-06 | Vicuron Pharm Inc | Bicykliske pyrrolidinforbindelser |
| AR036053A1 (es) | 2001-06-15 | 2004-08-04 | Versicor Inc | Compuestos de n-formil-hidroxilamina, un proceso para su preparacion y composiciones farmaceuticas |
| JP4494015B2 (ja) * | 2001-10-12 | 2010-06-30 | アゼヴァン ファーマスーティカルズ，インコーポレイテッド | β−ラクタミル・バソプレッシンＶ１ａ拮抗剤 |
| WO2003051314A2 (en) * | 2001-12-18 | 2003-06-26 | Medallion Biomedical, Llc | Antibiotic compounds |
| US20050282814A1 (en) * | 2002-10-03 | 2005-12-22 | Targegen, Inc. | Vasculostatic agents and methods of use thereof |
| WO2004030635A2 (en) * | 2002-10-03 | 2004-04-15 | Targegen, Inc. | Vasculostatic agents and methods of use thereof |
| TW200526651A (en) * | 2003-10-03 | 2005-08-16 | Serenix Pharmaceuticals Llc | 3-substituted β-lactamyl vasopressin V1a antagonists |
| EP1809614B1 (en) | 2004-04-08 | 2014-05-07 | TargeGen, Inc. | Benzotriazine inhibitors of kinases |
| PL382308A1 (pl) | 2004-08-25 | 2007-08-20 | Targegen, Inc. | Związki heterocykliczne i sposoby stosowania |
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| US4751299A (en) | 1983-11-18 | 1988-06-14 | Takeda Chemical Industries, Ltd. | Optically active β-lactams and method of their production |
| US4665171A (en) | 1985-07-17 | 1987-05-12 | Harvard University | Process and intermediates for β-lactam antibiotics |
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-
1997
- 1997-02-20 DK DK97907895T patent/DK0939632T3/da active
- 1997-02-20 AU AU19779/97A patent/AU1977997A/en not_active Abandoned
- 1997-02-20 WO PCT/US1997/003039 patent/WO1997030707A1/en not_active Ceased
- 1997-02-20 US US09/125,737 patent/US6204260B1/en not_active Expired - Lifetime
- 1997-02-20 EP EP97907895A patent/EP0939632B1/en not_active Expired - Lifetime
- 1997-02-20 DE DE69734321T patent/DE69734321T2/de not_active Expired - Lifetime
- 1997-02-20 CA CA002246753A patent/CA2246753C/en not_active Expired - Lifetime
- 1997-02-20 AT AT97907895T patent/ATE305781T1/de active
- 1997-02-20 JP JP52964797A patent/JP4212112B2/ja not_active Expired - Lifetime
- 1997-02-20 ES ES97907895T patent/ES2248840T3/es not_active Expired - Lifetime
-
2000
- 2000-12-08 US US09/733,430 patent/US6521611B2/en not_active Expired - Lifetime
-
2002
- 2002-12-20 US US10/327,240 patent/US6610680B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| ATE305781T1 (de) | 2005-10-15 |
| DE69734321D1 (de) | 2006-02-16 |
| AU1977997A (en) | 1997-09-10 |
| US6521611B2 (en) | 2003-02-18 |
| CA2246753C (en) | 2005-05-10 |
| EP0939632A4 (en) | 2002-09-25 |
| DK0939632T3 (da) | 2006-01-30 |
| DE69734321T2 (de) | 2006-08-10 |
| US20020049187A1 (en) | 2002-04-25 |
| EP0939632B1 (en) | 2005-10-05 |
| CA2246753A1 (en) | 1997-08-28 |
| JP2000504731A (ja) | 2000-04-18 |
| US6610680B1 (en) | 2003-08-26 |
| EP0939632A1 (en) | 1999-09-08 |
| WO1997030707A1 (en) | 1997-08-28 |
| JP4212112B2 (ja) | 2009-01-21 |
| US6204260B1 (en) | 2001-03-20 |
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