JP2003525850A5 - - Google Patents
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- JP2003525850A5 JP2003525850A5 JP2000531182A JP2000531182A JP2003525850A5 JP 2003525850 A5 JP2003525850 A5 JP 2003525850A5 JP 2000531182 A JP2000531182 A JP 2000531182A JP 2000531182 A JP2000531182 A JP 2000531182A JP 2003525850 A5 JP2003525850 A5 JP 2003525850A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- substituted
- group
- nrr
- alkyl
- 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.)
- Granted
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- 150000001875 compounds Chemical class 0.000 description 68
- 125000003118 aryl group Chemical group 0.000 description 25
- 125000001072 heteroaryl group Chemical group 0.000 description 25
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 21
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 21
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 18
- 229910052736 halogen Inorganic materials 0.000 description 13
- 150000002367 halogens Chemical class 0.000 description 13
- 125000003710 aryl alkyl group Chemical group 0.000 description 12
- 125000004446 heteroarylalkyl group Chemical group 0.000 description 12
- 125000004953 trihalomethyl group Chemical group 0.000 description 12
- 125000002877 alkyl aryl group Chemical group 0.000 description 11
- 125000000304 alkynyl group Chemical group 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 7
- -1 imidazol-2-yl-imidazolyl Chemical group 0.000 description 7
- 208000014674 injury Diseases 0.000 description 6
- 201000001119 neuropathy Diseases 0.000 description 6
- 230000007823 neuropathy Effects 0.000 description 6
- 208000033808 peripheral neuropathy Diseases 0.000 description 6
- 0 C=CC(*1)C1C(NCCC[C@@](C(N1[C@@]2CCC1)=O)NC2=O)=N Chemical compound C=CC(*1)C1C(NCCC[C@@](C(N1[C@@]2CCC1)=O)NC2=O)=N 0.000 description 5
- 125000003342 alkenyl group Chemical group 0.000 description 5
- 239000008194 pharmaceutical composition Substances 0.000 description 5
- BXRNXXXXHLBUKK-UHFFFAOYSA-N piperazine-2,5-dione Chemical group O=C1CNC(=O)CN1 BXRNXXXXHLBUKK-UHFFFAOYSA-N 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 210000003169 central nervous system Anatomy 0.000 description 4
- 230000001149 cognitive effect Effects 0.000 description 4
- 230000006378 damage Effects 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 125000000336 imidazol-5-yl group Chemical group [H]N1C([H])=NC([H])=C1[*] 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 208000000532 Chronic Brain Injury Diseases 0.000 description 3
- 229940123457 Free radical scavenger Drugs 0.000 description 3
- 208000027418 Wounds and injury Diseases 0.000 description 3
- 230000001154 acute effect Effects 0.000 description 3
- 210000004556 brain Anatomy 0.000 description 3
- 208000029028 brain injury Diseases 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 239000003937 drug carrier Substances 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 230000003446 memory effect Effects 0.000 description 3
- 239000000546 pharmaceutical excipient Substances 0.000 description 3
- 239000002516 radical scavenger Substances 0.000 description 3
- 210000000278 spinal cord Anatomy 0.000 description 3
- 230000008733 trauma Effects 0.000 description 3
- WSLYCILIEOFQPK-UHFFFAOYSA-N 3-methyl-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione Chemical compound O=C1C(C)NC(=O)C2CCCN21 WSLYCILIEOFQPK-UHFFFAOYSA-N 0.000 description 2
- XLUAWXQORJEMBD-UHFFFAOYSA-N Pyrrolo(1,2-a)pyrazine-1,4-dione, hexahydro-3-(1-methylethyl)- Chemical compound O=C1C(C(C)C)NC(=O)C2CCCN21 XLUAWXQORJEMBD-UHFFFAOYSA-N 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- 125000001041 indolyl group Chemical group 0.000 description 2
- SZJNCZMRZAUNQT-UHFFFAOYSA-N (3R,8aS)-hexahydro-3-(2-methylpropyl)pyrrolo[1,2-a]pyrazine-1,4-dione Natural products O=C1C(CC(C)C)NC(=O)C2CCCN21 SZJNCZMRZAUNQT-UHFFFAOYSA-N 0.000 description 1
- ZDACRNZBFJOLTC-UHFFFAOYSA-N (3S,6S)-3-[(1S)-1-methylpropyl]hexahydropyrrolo[1,2-a]pyrazine-1,4-dione Natural products O=C1C(C(C)CC)NC(=O)C2CCCN21 ZDACRNZBFJOLTC-UHFFFAOYSA-N 0.000 description 1
- FRJJJAKBRKABFA-TYFAACHXSA-N (4r,6s)-6-[(e)-2-[6-chloro-4-(4-fluorophenyl)-2-propan-2-ylquinolin-3-yl]ethenyl]-4-hydroxyoxan-2-one Chemical compound C(\[C@H]1OC(=O)C[C@H](O)C1)=C/C=1C(C(C)C)=NC2=CC=C(Cl)C=C2C=1C1=CC=C(F)C=C1 FRJJJAKBRKABFA-TYFAACHXSA-N 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- DPRJPRMZJGWLHY-HNGSOEQISA-N (e,3r,5s)-7-[5-(4-fluorophenyl)-3-propan-2-yl-1-pyrazin-2-ylpyrazol-4-yl]-3,5-dihydroxyhept-6-enoic acid Chemical compound OC(=O)C[C@H](O)C[C@H](O)/C=C/C=1C(C(C)C)=NN(C=2N=CC=NC=2)C=1C1=CC=C(F)C=C1 DPRJPRMZJGWLHY-HNGSOEQISA-N 0.000 description 1
- YKYWUHHZZRBGMG-JWTNVVGKSA-N 1-methyl-2-[[(1r,5s)-6-[[5-(trifluoromethyl)pyridin-2-yl]methoxymethyl]-3-azabicyclo[3.1.0]hexan-3-yl]methyl]benzimidazole Chemical compound C1([C@@H]2CN(C[C@@H]21)CC=1N(C2=CC=CC=C2N=1)C)COCC1=CC=C(C(F)(F)F)C=N1 YKYWUHHZZRBGMG-JWTNVVGKSA-N 0.000 description 1
- QZBUWPVZSXDWSB-UHFFFAOYSA-N 3'-Acetamido-3'-deoxyadenosin Natural products O=C1N2CCCC2C(=O)NC1CC1=CC=CC=C1 QZBUWPVZSXDWSB-UHFFFAOYSA-N 0.000 description 1
- KUZSBKJSGSKPJH-VXGBXAGGSA-N 5-[(9R)-6-[(3R)-3-methylmorpholin-4-yl]-11-oxa-1,3,5-triazatricyclo[7.4.0.02,7]trideca-2,4,6-trien-4-yl]pyrazin-2-amine Chemical compound C[C@@H]1COCCN1c1nc(nc2N3CCOC[C@H]3Cc12)-c1cnc(N)cn1 KUZSBKJSGSKPJH-VXGBXAGGSA-N 0.000 description 1
- LDIOUQIXNSSOGU-UHFFFAOYSA-N 8-(3-pentylamino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-6,7-dihydro-5h-cyclopenta[d]pyrazolo[1,5-a]pyrimidine Chemical compound CC1=NN2C(NC(CC)CC)=C3CCCC3=NC2=C1C1=CC=C(OC)C=C1Cl LDIOUQIXNSSOGU-UHFFFAOYSA-N 0.000 description 1
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- QUMCIHKVKQYNPA-RUZDIDTESA-N C1(CCCCC1)CN1[C@@H](C=2N(C=3C=NC(=NC1=3)NC1=C(C=C(C(=O)NC3CCN(CC3)C)C=C1)OC)C(=NN=2)C)CC Chemical compound C1(CCCCC1)CN1[C@@H](C=2N(C=3C=NC(=NC1=3)NC1=C(C=C(C(=O)NC3CCN(CC3)C)C=C1)OC)C(=NN=2)C)CC QUMCIHKVKQYNPA-RUZDIDTESA-N 0.000 description 1
- LDUBWSIVHANZFZ-IUCAKERBSA-N CC(C)(C)SC[C@@H](C(N1[C@H]2CCC1)=O)NC2=O Chemical compound CC(C)(C)SC[C@@H](C(N1[C@H]2CCC1)=O)NC2=O LDUBWSIVHANZFZ-IUCAKERBSA-N 0.000 description 1
- LSGOTAXPWMCUCK-UHFFFAOYSA-N D-prolyl-L-tyrosine anhydride Natural products C1=CC(O)=CC=C1CC1C(=O)N2CCCC2C(=O)N1 LSGOTAXPWMCUCK-UHFFFAOYSA-N 0.000 description 1
- QQKRRCFJMUFQSQ-QWRGUYRKSA-N N/C(/NCCC[C@@H](C(N1[C@H]2CCC1)=O)NC2=O)=N/C1CC1 Chemical compound N/C(/NCCC[C@@H](C(N1[C@H]2CCC1)=O)NC2=O)=N/C1CC1 QQKRRCFJMUFQSQ-QWRGUYRKSA-N 0.000 description 1
- GOFVWXHQOCJXJK-BRHZVYESSA-N N=C(NCC[C@H](C1)C1(C(N1[C@H]2CCC1)=O)NC2=O)S Chemical compound N=C(NCC[C@H](C1)C1(C(N1[C@H]2CCC1)=O)NC2=O)S GOFVWXHQOCJXJK-BRHZVYESSA-N 0.000 description 1
- UJYOQFVXMWIEBX-LURJTMIESA-N O=C([C@H]1N2CCC1)NC1(CC1)C2=O Chemical compound O=C([C@H]1N2CCC1)NC1(CC1)C2=O UJYOQFVXMWIEBX-LURJTMIESA-N 0.000 description 1
- QTPGVDQFVSPTGL-VIFPVBQESA-N O=C([C@H]1N2CCC1)NC1(CCCCC1)C2=O Chemical compound O=C([C@H]1N2CCC1)NC1(CCCCC1)C2=O QTPGVDQFVSPTGL-VIFPVBQESA-N 0.000 description 1
- GLEOIKLQBZNKJZ-WDSKDSINSA-N Pro-Asp Chemical compound OC(=O)C[C@@H](C(O)=O)NC(=O)[C@@H]1CCCN1 GLEOIKLQBZNKJZ-WDSKDSINSA-N 0.000 description 1
- BEPSGCXDIVACBU-IUCAKERBSA-N Pro-His Chemical compound C([C@@H](C(=O)O)NC(=O)[C@H]1NCCC1)C1=CN=CN1 BEPSGCXDIVACBU-IUCAKERBSA-N 0.000 description 1
- RVQDZELMXZRSSI-IUCAKERBSA-N Pro-Lys Chemical compound NCCCC[C@@H](C(O)=O)NC(=O)[C@@H]1CCCN1 RVQDZELMXZRSSI-IUCAKERBSA-N 0.000 description 1
- UEKYKRQIAQHOOZ-KBPBESRZSA-N Pro-Trp Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)[O-])C(=O)[C@@H]1CCC[NH2+]1 UEKYKRQIAQHOOZ-KBPBESRZSA-N 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- AEULIVPVIDOLIN-UHFFFAOYSA-N cep-11981 Chemical compound C1=C2C3=C4CNC(=O)C4=C4C5=CN(C)N=C5CCC4=C3N(CC(C)C)C2=CC=C1NC1=NC=CC=N1 AEULIVPVIDOLIN-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- SZJNCZMRZAUNQT-IUCAKERBSA-N cyclo(L-Leu-L-Pro) Chemical compound O=C1[C@H](CC(C)C)NC(=O)[C@@H]2CCCN21 SZJNCZMRZAUNQT-IUCAKERBSA-N 0.000 description 1
- QZBUWPVZSXDWSB-RYUDHWBXSA-N cyclo(L-Phe-L-Pro) Chemical compound C([C@@H]1NC([C@@H]2CCCN2C1=O)=O)C1=CC=CC=C1 QZBUWPVZSXDWSB-RYUDHWBXSA-N 0.000 description 1
- 108010076347 cyclo(prolyl-leucyl) Proteins 0.000 description 1
- 108010007383 cyclo(prolyl-valyl) Proteins 0.000 description 1
- 108010014087 cyclo(prolylarginyl) Proteins 0.000 description 1
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 description 1
- LSGOTAXPWMCUCK-RYUDHWBXSA-N maculosin Chemical compound C1=CC(O)=CC=C1C[C@H]1C(=O)N2CCC[C@H]2C(=O)N1 LSGOTAXPWMCUCK-RYUDHWBXSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical compound ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 description 1
- 230000004770 neurodegeneration Effects 0.000 description 1
- 208000015122 neurodegenerative disease Diseases 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- FRACPXUHUTXLCX-BELIEFIBSA-N tert-butyl N-{1-[(1S)-1-{[(1R,2S)-1-(benzylcarbamoyl)-1-hydroxy-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl]carbamoyl}-2-cyclopropylethyl]-2-oxopyridin-3-yl}carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=CN(C1=O)[C@@H](CC2CC2)C(=O)N[C@@H](C[C@@H]3CCNC3=O)[C@H](C(=O)NCC4=CC=CC=C4)O FRACPXUHUTXLCX-BELIEFIBSA-N 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2218498A | 1998-02-11 | 1998-02-11 | |
| US09/022,184 | 1998-02-11 | ||
| US9578898P | 1998-08-07 | 1998-08-07 | |
| US60/095,788 | 1998-08-07 | ||
| US09/246,307 US7202279B1 (en) | 1998-02-11 | 1999-02-08 | Cyclic dipeptides and azetidinone compounds and their use in treating CNS injury and neurodegenerative disorders |
| US09/246,307 | 1999-02-08 | ||
| PCT/US1999/003147 WO1999040931A1 (en) | 1998-02-11 | 1999-02-10 | Cyclic dipeptides and azetidinone compounds and their use in treating cns injury and neurodegenerative disorders |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2003525850A JP2003525850A (ja) | 2003-09-02 |
| JP2003525850A5 true JP2003525850A5 (https=) | 2006-01-05 |
| JP4443763B2 JP4443763B2 (ja) | 2010-03-31 |
Family
ID=27361814
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000531182A Expired - Fee Related JP4443763B2 (ja) | 1998-02-11 | 1999-02-10 | 環式ジペプチドおよびアゼチジノン並びにｃｎｓ損傷および神経変性疾患の治療におけるそれらの使用 |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US7202279B1 (https=) |
| EP (1) | EP1061936A4 (https=) |
| JP (1) | JP4443763B2 (https=) |
| AU (1) | AU774681B2 (https=) |
| CA (1) | CA2320378A1 (https=) |
| WO (1) | WO1999040931A1 (https=) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6605623B1 (en) | 1998-12-18 | 2003-08-12 | Bristol-Myers Squibb Pharma Co. | N-ureidoalkyl-piperidines as modulators of chemokine receptor activity |
| WO2002011676A2 (en) | 2000-08-04 | 2002-02-14 | Dmi Biosciences, Inc. | Method of using diketopiperazines and composition containing them |
| AU2001284697A1 (en) | 2000-08-04 | 2002-02-18 | Dmi Biosciences, Inc. | Method of synthesizing diketopiperazines |
| NZ539735A (en) | 2002-10-02 | 2009-07-31 | Dmi Biosciences Inc | Diagnosis and monitoring of diseases using markers, such as diketopiperazines |
| US7335644B2 (en) * | 2003-03-31 | 2008-02-26 | Council Of Scientific And Industrial Research | Anti-hypertensive molecules and process for preparation thereof |
| EP1622633B1 (en) | 2003-05-15 | 2016-02-24 | Ampio Pharmaceuticals, Inc. | Treatment of t-cell mediated diseases |
| US8519127B2 (en) | 2003-09-03 | 2013-08-27 | Mike John Bickerdike | Cyclic glycyl-2-allyl proline and its use in treatment of peripheral neuropathy |
| US8791117B2 (en) | 2003-09-03 | 2014-07-29 | Neuren Pharmaceuticals Limited | Cyclic glycyl-2-allyl proline improves cognitive performance in impaired animals |
| JP4842817B2 (ja) * | 2003-09-03 | 2011-12-21 | ニューレン ファーマシューティカルズ リミテッド | 神経保護二環式化合物およびその使用方法 |
| KR101530050B1 (ko) * | 2007-03-02 | 2015-06-22 | 주식회사 노브메타파마 | 알츠하이머 질환 및 치매를 치료하기 위한 조성물 및 방법 |
| WO2009100431A1 (en) * | 2008-02-07 | 2009-08-13 | Marquette University | Cysteine and cystine prodrugs to treat schizophrenia and reduce drug cravings |
| EP2300011A4 (en) | 2008-05-27 | 2012-06-20 | Dmi Life Sciences Inc | THERAPEUTIC PROCESSES AND COMPOUNDS |
| KR101137503B1 (ko) * | 2009-07-14 | 2012-04-20 | 웰이앤씨 주식회사 | 고분자 고체 지지체를 이용한 히스티딜-프롤린아미드 유도체의 제조 방법 |
| JP5058379B2 (ja) | 2009-12-25 | 2012-10-24 | サントリーホールディングス株式会社 | 学習意欲改善剤 |
| CA2810844C (en) | 2010-09-07 | 2017-03-21 | Dmi Acquisition Corp. | Diketopiperazine compositions for the treatment of metabolic syndrome and related conditions |
| EP3721884A1 (en) | 2011-10-10 | 2020-10-14 | Ampio Pharmaceuticals, Inc. | Treatment of degenerative joint disease with da-dkp (= aspartyl-alanyl diketopiperazine) |
| SG10201608087WA (en) | 2011-10-10 | 2016-11-29 | Ampio Pharmaceuticals Inc | Implantable medical devices with increased immune tolerance, and methods for making and implanting |
| CN103841974A (zh) | 2011-10-28 | 2014-06-04 | 安皮奥制药股份有限公司 | 鼻炎的治疗 |
| JP6465803B2 (ja) * | 2012-10-22 | 2019-02-06 | シティ・オブ・ホープＣｉｔｙ ｏｆ Ｈｏｐｅ | Ｅｔｐ誘導体 |
| CA2906864A1 (en) | 2013-03-15 | 2014-09-18 | Ampio Pharmaceuticals, Inc. | Compositions for the mobilization, homing, expansion and differentiation of stem cells and methods of using the same |
| CA2958080A1 (en) | 2014-08-18 | 2016-02-25 | Ampio Pharmaceuticals, Inc. | Treatment of joint conditions |
| US11389512B2 (en) | 2015-06-22 | 2022-07-19 | Ampio Pharmaceuticals, Inc. | Use of low molecular weight fractions of human serum albumin in treating diseases |
| JPWO2017119481A1 (ja) * | 2016-01-08 | 2018-11-08 | サントリーホールディングス株式会社 | 環状ジペプチド含有神経性疾患予防用組成物 |
| KR20240155382A (ko) * | 2016-05-26 | 2024-10-28 | 가부시키가이샤 아미노 압 | 수면 개선제 |
| CA3029109A1 (en) | 2016-06-29 | 2018-01-04 | Orion Corporation | Benzodioxane derivatives and their pharmaceutical use |
| EP3512520B1 (en) | 2016-09-15 | 2023-06-21 | City of Hope | Dithio derivatives of epidithiodiketopiperazine (etp) |
| JP7020797B2 (ja) * | 2017-04-25 | 2022-02-16 | キリンホールディングス株式会社 | 自律神経調節用組成物 |
| US11820834B2 (en) | 2018-07-10 | 2023-11-21 | Novmetapharma Co., Ltd. | Polymorphic forms of Cyclo (-His-Pro) and methods of use to treat kidney disease |
| CN112424215B (zh) * | 2018-07-10 | 2024-12-31 | 诺麦塔制药有限公司 | 环(-his-pro)的新多晶型形式 |
| KR102140910B1 (ko) | 2019-03-28 | 2020-08-04 | 주식회사 노브메타파마 | Chp(사이클로-히스프로)를 포함하는 섬유증의 예방, 개선 또는 치료용 조성물 |
| WO2021195265A1 (en) | 2020-03-24 | 2021-09-30 | Ampio Pharmaceuticals, Inc. | Methods for treating diseases associated with respiratory viruses |
| US12053467B2 (en) * | 2020-12-18 | 2024-08-06 | NovMeta Pharma Co., Ltd. | Method of treating fibrosis |
| JPWO2024262349A1 (https=) * | 2023-06-19 | 2024-12-26 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1583797A (https=) * | 1967-04-12 | 1969-12-05 | ||
| CS231227B1 (en) * | 1982-10-01 | 1984-10-15 | Evzen Kasafirek | 2,5-pierazindion derivatives |
| CA1256650A (en) * | 1983-03-25 | 1989-06-27 | Toshinari Tamura | Process of producing 2-azetidinone-4-substituted compounds, and medicaments containing the compounds |
| WO1994006794A1 (en) * | 1992-09-24 | 1994-03-31 | National Institutes Of Health | Aralkyl diazabicycloalkane derivatives for cns disorders |
| FI942400L (fi) | 1993-05-25 | 1994-11-26 | Daiichi Seiyaku Co | Lääkeaine hermosairauksia vastaan |
| US5859001A (en) | 1996-01-11 | 1999-01-12 | University Of Florida Research Foundation, Inc. | Neuroprotective effects of polycyclic phenolic compounds |
| JP3122589B2 (ja) * | 1994-12-29 | 2001-01-09 | 株式会社タカトリ | パンティストッキング素材の装着方法 |
| US6310052B1 (en) | 1996-06-04 | 2001-10-30 | Queen's University At Kingston | Nitrate esters and their use for neurological conditions |
| GB9915437D0 (en) | 1999-07-01 | 1999-09-01 | Cerebrus Ltd | Chemical compounds III |
-
1999
- 1999-02-08 US US09/246,307 patent/US7202279B1/en not_active Expired - Fee Related
- 1999-02-10 JP JP2000531182A patent/JP4443763B2/ja not_active Expired - Fee Related
- 1999-02-10 EP EP99909487A patent/EP1061936A4/en not_active Withdrawn
- 1999-02-10 CA CA002320378A patent/CA2320378A1/en not_active Abandoned
- 1999-02-10 WO PCT/US1999/003147 patent/WO1999040931A1/en not_active Ceased
- 1999-02-10 AU AU28678/99A patent/AU774681B2/en not_active Ceased
-
2007
- 2007-02-22 US US11/709,456 patent/US8044103B2/en not_active Expired - Fee Related
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