NZ538058A - Quinuclidine derivatives and their use for treating disorders related to CNS and PNS - Google Patents
Quinuclidine derivatives and their use for treating disorders related to CNS and PNSInfo
- Publication number
- NZ538058A NZ538058A NZ538058A NZ53805803A NZ538058A NZ 538058 A NZ538058 A NZ 538058A NZ 538058 A NZ538058 A NZ 538058A NZ 53805803 A NZ53805803 A NZ 53805803A NZ 538058 A NZ538058 A NZ 538058A
- Authority
- NZ
- New Zealand
- Prior art keywords
- alkoxy
- alkyl
- aza
- octane
- cycloalkoxy
- Prior art date
Links
- 150000008584 quinuclidines Chemical class 0.000 title abstract description 22
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 98
- 150000001875 compounds Chemical class 0.000 claims abstract description 82
- 201000010099 disease Diseases 0.000 claims abstract description 56
- 208000035475 disorder Diseases 0.000 claims abstract description 42
- 238000011282 treatment Methods 0.000 claims abstract description 26
- 239000000126 substance Substances 0.000 claims abstract description 16
- 208000002193 Pain Diseases 0.000 claims abstract description 14
- 210000003169 central nervous system Anatomy 0.000 claims abstract description 11
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims abstract description 8
- 239000003814 drug Substances 0.000 claims abstract description 8
- 230000004770 neurodegeneration Effects 0.000 claims abstract description 7
- 230000016160 smooth muscle contraction Effects 0.000 claims abstract description 7
- -1 5,6,7,8-tetrahydro-naphthyl Chemical group 0.000 claims description 155
- 150000003839 salts Chemical class 0.000 claims description 65
- UANSQQFYKHHDJM-KRWDZBQOSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]naphthalene-1-carboxamide Chemical compound C1=CC=C2C(C(N[C@@H]3C4CCN(CC4)C3)=O)=CC=CC2=C1 UANSQQFYKHHDJM-KRWDZBQOSA-N 0.000 claims description 57
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 57
- 239000000203 mixture Substances 0.000 claims description 49
- 125000003367 polycyclic group Chemical group 0.000 claims description 49
- 125000002950 monocyclic group Chemical group 0.000 claims description 44
- 125000000623 heterocyclic group Chemical group 0.000 claims description 43
- 125000001424 substituent group Chemical group 0.000 claims description 38
- 125000002837 carbocyclic group Chemical group 0.000 claims description 35
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 35
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 26
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 24
- 125000003368 amide group Chemical group 0.000 claims description 21
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 20
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 17
- 239000008194 pharmaceutical composition Substances 0.000 claims description 14
- CPRRHERYRRXBRZ-SRVKXCTJSA-N methyl n-[(2s)-1-[[(2s)-1-hydroxy-3-[(3s)-2-oxopyrrolidin-3-yl]propan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate Chemical compound COC(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CO)C[C@@H]1CCNC1=O CPRRHERYRRXBRZ-SRVKXCTJSA-N 0.000 claims description 12
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 11
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 11
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 10
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 claims description 10
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 9
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 9
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 9
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims description 8
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 7
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 7
- 230000002265 prevention Effects 0.000 claims description 7
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 7
- 102000005962 receptors Human genes 0.000 claims description 7
- 108020003175 receptors Proteins 0.000 claims description 7
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 6
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 6
- 125000003828 azulenyl group Chemical group 0.000 claims description 6
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 6
- 125000001041 indolyl group Chemical group 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 6
- 125000004159 quinolin-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C([H])C(*)=NC2=C1[H] 0.000 claims description 6
- 125000004549 quinolin-4-yl group Chemical group N1=CC=C(C2=CC=CC=C12)* 0.000 claims description 6
- 125000004550 quinolin-6-yl group Chemical group N1=CC=CC2=CC(=CC=C12)* 0.000 claims description 6
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 6
- 125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 claims description 6
- 125000000335 thiazolyl group Chemical group 0.000 claims description 6
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 5
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 5
- UYDJFXWILYZAEM-UHFFFAOYSA-N 3-(6-bromopyridazin-3-yl)oxy-1-azabicyclo[2.2.2]octane Chemical compound N1=NC(Br)=CC=C1OC1C(CC2)CCN2C1 UYDJFXWILYZAEM-UHFFFAOYSA-N 0.000 claims description 5
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 claims description 5
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 5
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 5
- 125000004262 quinoxalin-2-yl group Chemical group [H]C1=NC2=C([H])C([H])=C([H])C([H])=C2N=C1* 0.000 claims description 5
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- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims description 5
- 125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 claims description 5
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims description 4
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- LRQZHEAZRKGYRO-UHFFFAOYSA-N 2-(1-azabicyclo[2.2.2]octan-3-yloxy)quinoline Chemical compound C1=CC=CC2=NC(OC3C4CCN(C3)CC4)=CC=C21 LRQZHEAZRKGYRO-UHFFFAOYSA-N 0.000 claims description 3
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- ONZZUKINKMKNFG-UHFFFAOYSA-N 2-(1-azabicyclo[2.2.2]octan-3-yloxy)-1,3-benzoxazole Chemical compound C1=CC=C2OC(OC3C4CCN(C3)CC4)=NC2=C1 ONZZUKINKMKNFG-UHFFFAOYSA-N 0.000 claims description 2
- BXENYFDBSRHICB-UHFFFAOYSA-N 2-(1-azabicyclo[2.2.2]octan-3-yloxy)-3-chloroquinoxaline Chemical compound C1N(CC2)CCC2C1OC1=NC2=CC=CC=C2N=C1Cl BXENYFDBSRHICB-UHFFFAOYSA-N 0.000 claims description 2
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- ZLMJMSJWJFRBEC-OUBTZVSYSA-N potassium-40 Chemical compound [40K] ZLMJMSJWJFRBEC-OUBTZVSYSA-N 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
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- 229940002612 prodrug Drugs 0.000 description 1
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- OVYWMEWYEJLIER-UHFFFAOYSA-N quinolin-6-ol Chemical compound N1=CC=CC2=CC(O)=CC=C21 OVYWMEWYEJLIER-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 230000000862 serotonergic effect Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229940075554 sorbate Drugs 0.000 description 1
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- 239000004334 sorbic acid Substances 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- GTZCVFVGUGFEME-UHFFFAOYSA-N trans-aconitic acid Natural products OC(=O)CC(C(O)=O)=CC(O)=O GTZCVFVGUGFEME-UHFFFAOYSA-N 0.000 description 1
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Classifications
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Landscapes
- Health & Medical Sciences (AREA)
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- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DKPA200201208 | 2002-08-14 | ||
| DKPA200201472 | 2002-10-02 | ||
| PCT/DK2003/000538 WO2004016608A1 (en) | 2002-08-14 | 2003-08-13 | Novel quinuclidine derivatives and their use |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ538058A true NZ538058A (en) | 2006-11-30 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| NZ538058A NZ538058A (en) | 2002-08-14 | 2003-08-13 | Quinuclidine derivatives and their use for treating disorders related to CNS and PNS |
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| EP (2) | EP1905771A3 (enExample) |
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| KR (1) | KR20050055711A (enExample) |
| CN (1) | CN100513406C (enExample) |
| AT (1) | ATE384720T1 (enExample) |
| AU (1) | AU2003250322B2 (enExample) |
| BR (1) | BR0313153A (enExample) |
| CA (1) | CA2493245A1 (enExample) |
| DE (1) | DE60318860T2 (enExample) |
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| IS (1) | IS7742A (enExample) |
| MX (1) | MXPA05001702A (enExample) |
| NO (1) | NO20051264L (enExample) |
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| JPS6262265A (ja) * | 1985-09-13 | 1987-03-18 | Hitachi Ltd | 復水器自動検査補修システム |
| DE10164139A1 (de) | 2001-12-27 | 2003-07-10 | Bayer Ag | 2-Heteroarylcarbonsäureamide |
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| EP1603585A2 (en) | 2003-03-14 | 2005-12-14 | Bristol-Myers Squibb Company | Polynucleotide encoding a novel human g-protein coupled receptor variant of hm74, hgprbmy74 |
| DE602004031124D1 (de) * | 2003-08-13 | 2011-03-03 | Neurosearch As | Neue chinuklidinderivative und deren pharmazeutische verwendung |
| US7160876B2 (en) | 2003-12-22 | 2007-01-09 | Abbott Laboratories | Fused bicycloheterocycle substituted quinuclidine derivatives |
| US7309699B2 (en) | 2003-12-22 | 2007-12-18 | Abbott Laboratories | 3-Quinuclidinyl amino-substituted biaryl derivatives |
| US7655657B2 (en) | 2003-12-22 | 2010-02-02 | Abbott Laboratories | Fused bicycloheterocycle substituted quinuclidine derivatives |
| US7241773B2 (en) | 2003-12-22 | 2007-07-10 | Abbott Laboratories | 3-quinuclidinyl heteroatom bridged biaryl derivatives |
| US20050137203A1 (en) * | 2003-12-22 | 2005-06-23 | Jianguo Ji | 3-quinuclidinyl amino-substituted biaryl derivatives |
| US20050245531A1 (en) * | 2003-12-22 | 2005-11-03 | Abbott Laboratories | Fused bicycloheterocycle substituted quinuclidine derivatives |
| US20050137398A1 (en) * | 2003-12-22 | 2005-06-23 | Jianguo Ji | 3-Quinuclidinyl heteroatom bridged biaryl derivatives |
| EP1824848A1 (en) * | 2004-12-10 | 2007-08-29 | Abbott Laboratories | Fused bicycloheterocycle substituted quinuclidine derivatives |
| US7365193B2 (en) | 2004-02-04 | 2008-04-29 | Abbott Laboratories | Amino-substituted tricyclic derivatives and methods of use |
| US20050171079A1 (en) * | 2004-02-04 | 2005-08-04 | Schrimpf Michael R. | Amino-substituted tricyclic derivatives and methods of use |
| SE0400970D0 (sv) * | 2004-04-14 | 2004-04-14 | Astrazeneca Ab | Nicotinic acetylcholine receptor ligands |
| PE20060437A1 (es) | 2004-06-18 | 2006-06-08 | Novartis Ag | COMPUESTOS AZA-BICICLONONANOS COMO LIGANDOS COLINERGICOS DE nAChR |
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| GB0424564D0 (en) | 2004-11-05 | 2004-12-08 | Novartis Ag | Organic compounds |
| CA2591817A1 (en) * | 2004-12-22 | 2006-06-29 | Memory Pharmaceuticals Corporation | Nicotinic alpha-7 receptor ligands and preparation and uses thereof |
| BRPI0617534A2 (pt) * | 2005-09-23 | 2011-07-26 | Memory Pharm Corp | Composto, composição farmacêutica, método para a ativação/estimulação seletiva de receptores nicotínicos de a-7 em um paciente, método para o tratamento de um paciente que sofre de uma doença psicótica, uma doença neurodegenerativa que envolve uma disfunção do sistema colinérgico, e/ou uma condição de degeneração da memória e/ou da cognição, método para o tratamento de um paciente que sofre de demência e/ou uma outra condição com perda da memória, método para o tratamento de um paciente que sofre de degeneração da memória devida à degeneração cognitiva suave devida ao envelhecimento, mal de alzheimer, esquizofrenia, mal de parkinson, mal de huntington, mal de pick, mal de creutzfeldt-jakob, depressão, envelhecimento, trauma na cabeça, acidente vascular cerebral, hipoxia do cns, senilidade cerebral, demência de multiinfarto, hiv e/ou doença cardiovascular, método para o tratamento e/ou a prevenção da demência em um paciente com mal de alzheimer, método para o tratamento de um paciente para a retirada do álcool ou para o tratamento de um paciente com terapia anti-intoxicação, método para o tratamento de um paciente para conferir neuroproteção contra os danos associados com acidentes vasculares cerebrais e isquemia e excitotoxicidade induzida por glutamato, método para o tratamento de um paciente que sofre de vício de nicotina, dor, tontura de fuso horário, obesidade e/ou diabetes, método de indução de um paciente a parar de fumar, método para o tratamento de um paciente que sofre de degeneração cognitiva suave (mci), demência vascular (vad), declínio cognitivo associado com a idade (aacd), amnésia associada com a cirurgia de coração aberto, apreensão cardíaca, anestesia geral, déficits da memória devido à exposição a agentes anestésicos(...) |
| GB0521508D0 (en) * | 2005-10-21 | 2005-11-30 | Novartis Ag | Organic compounds |
| GB0525672D0 (en) * | 2005-12-16 | 2006-01-25 | Novartis Ag | Organic compounds |
| GB0525673D0 (en) * | 2005-12-16 | 2006-01-25 | Novartis Ag | Organic compounds |
| FR2904002A1 (fr) * | 2006-07-19 | 2008-01-25 | Galderma Res & Dev S N C Snc | Modulateurs de la lanosterol synthetase dans le traitement de l'acne ou de l'hyperseborrhee |
| US8314119B2 (en) | 2006-11-06 | 2012-11-20 | Abbvie Inc. | Azaadamantane derivatives and methods of use |
| SA08290475B1 (ar) | 2007-08-02 | 2013-06-22 | Targacept Inc | (2s، 3r)-n-(2-((3-بيردينيل)ميثيل)-1-آزا بيسيكلو[2، 2، 2]أوكت-3-يل)بنزو فيوران-2-كربوكساميد، وصور أملاحه الجديدة وطرق استخدامه |
| US8383657B2 (en) | 2007-12-21 | 2013-02-26 | Abbott Laboratories | Thiazolylidine urea and amide derivatives and methods of use thereof |
| TW201031664A (en) | 2009-01-26 | 2010-09-01 | Targacept Inc | Preparation and therapeutic applications of (2S,3R)-N-2-((3-pyridinyl)methyl)-1-azabicyclo[2.2.2]oct-3-yl)-3,5-difluorobenzamide |
| WO2011009890A2 (en) * | 2009-07-23 | 2011-01-27 | Novartis Ag | Use of azabicycloalkyl derivatives or pyrrolidine-2-one derivatives |
| JO3250B1 (ar) | 2009-09-22 | 2018-09-16 | Novartis Ag | إستعمال منشطات مستقبل نيكوتينيك أسيتيل كولين ألفا 7 |
| PT3029039T (pt) | 2010-05-17 | 2017-11-28 | Forum Pharmaceuticals Inc | Formulações farmacêuticas que compreendem formas cristalinas de cloridrato de (r)-7-cloro-n-(quinuclidin-3-il)benzo(b)tiofeno-2-carboxamida mono-hidratado |
| PE20131394A1 (es) | 2010-09-23 | 2014-01-11 | Abbvie Inc | Monohidrato de derivados de aza-adamantano |
| US20120220729A1 (en) * | 2011-02-28 | 2012-08-30 | Boehringer Ingelheim International Gmbh | Liquid phase separation of plasmid dna isoforms and topoisomers |
| EP2846796A4 (en) | 2012-05-08 | 2015-10-21 | Forum Pharmaceuticals Inc | METHODS OF MAINTAINING, PROCESSING OR ENHANCING COGNITIVE FUNCTION |
| WO2014111837A1 (en) * | 2013-01-15 | 2014-07-24 | Novartis Ag | Use of alpha 7 nicotinic acetylcholine receptor agonists |
| US20150313884A1 (en) | 2013-01-15 | 2015-11-05 | Novartis Ag | Use of alpha 7 nicotinic acetylcholine receptor agonists |
| BR112015016994A8 (pt) * | 2013-01-15 | 2018-01-23 | Novartis Ag | uso de agonistas do receptor alfa 7 nicotínico de acetilcolina |
| WO2016100184A1 (en) | 2014-12-16 | 2016-06-23 | Forum Pharmaceuticals, Inc. | Geminal substituted quinuclidine amide compounds as agonists of alpha-7 nicotinic acetylcholine receptors |
| WO2016201096A1 (en) | 2015-06-10 | 2016-12-15 | Forum Pharmaceuticals, Inc. | Aminobenzisoxazole compounds as agonists of a7-nicotinic acetylcholine receptors |
| WO2017027600A1 (en) | 2015-08-12 | 2017-02-16 | Forum Pharmaceuticals, Inc. | GEMINAL SUBSTITUTED AMINOBENZISOXAZOLE COMPOUNDS AS AGONISTS OF α7-NICOTINIC ACETYLCHOLINE RECEPTORS |
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| US3534053A (en) * | 1967-05-24 | 1970-10-13 | American Home Prod | Quinuclidine derivatives |
| SU495310A1 (ru) * | 1974-03-05 | 1975-12-15 | Всесоюзный Научно-Исследовательский Химико-Фармацевтический Институт Им.С.Орджоникидзе | Хинуклидил-3-диарал(гетерил) карбинолы, про вл ющие антигистаминную, антисеротониновую и антиаллергическую активность и способ их получени |
| DE3718317A1 (de) * | 1986-12-10 | 1988-06-16 | Bayer Ag | Substituierte basische 2-aminotetraline |
| CA1307790C (en) * | 1987-08-04 | 1992-09-22 | Ian Anthony Cliffe | Ethers |
| US5405853A (en) * | 1987-09-10 | 1995-04-11 | Merck Sharpe & Dohme Ltd. | Thiadiazoles useful in the treatment of senile dementia |
| JP2752143B2 (ja) * | 1988-04-01 | 1998-05-18 | 三共株式会社 | カルバペネム誘導体 |
| EP0363085A3 (en) * | 1988-10-03 | 1991-03-27 | Beecham Group Plc | Novel compounds |
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| EP0555478A4 (en) * | 1990-08-31 | 1993-11-18 | Nippon Shinyaku Company, Limited | Pyrimidine derivative and medicine |
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-
2003
- 2003-08-13 RU RU2005101748/04A patent/RU2323217C2/ru not_active IP Right Cessation
- 2003-08-13 WO PCT/DK2003/000538 patent/WO2004016608A1/en not_active Ceased
- 2003-08-13 NZ NZ538058A patent/NZ538058A/en not_active IP Right Cessation
- 2003-08-13 AU AU2003250322A patent/AU2003250322B2/en not_active Ceased
- 2003-08-13 US US10/522,150 patent/US20050245567A1/en not_active Abandoned
- 2003-08-13 PL PL03375533A patent/PL375533A1/xx not_active Application Discontinuation
- 2003-08-13 AT AT03787742T patent/ATE384720T1/de not_active IP Right Cessation
- 2003-08-13 EP EP08100204A patent/EP1905771A3/en not_active Withdrawn
- 2003-08-13 CN CNB038190788A patent/CN100513406C/zh not_active Expired - Fee Related
- 2003-08-13 EP EP03787742A patent/EP1532144B1/en not_active Expired - Lifetime
- 2003-08-13 CA CA002493245A patent/CA2493245A1/en not_active Abandoned
- 2003-08-13 DE DE60318860T patent/DE60318860T2/de not_active Expired - Lifetime
- 2003-08-13 MX MXPA05001702A patent/MXPA05001702A/es active IP Right Grant
- 2003-08-13 BR BR0313153-0A patent/BR0313153A/pt not_active IP Right Cessation
- 2003-08-13 JP JP2005502013A patent/JP2005538187A/ja active Pending
- 2003-08-13 KR KR1020057002514A patent/KR20050055711A/ko not_active Ceased
-
2005
- 2005-01-12 IL IL16625405A patent/IL166254A0/xx unknown
- 2005-03-11 NO NO20051264A patent/NO20051264L/no not_active Application Discontinuation
- 2005-03-14 IS IS7742A patent/IS7742A/is unknown
-
2008
- 2008-09-08 US US12/206,302 patent/US20090005390A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| EP1532144B1 (en) | 2008-01-23 |
| RU2323217C2 (ru) | 2008-04-27 |
| MXPA05001702A (es) | 2005-04-19 |
| CN100513406C (zh) | 2009-07-15 |
| DE60318860T2 (de) | 2008-05-21 |
| RU2005101748A (ru) | 2006-01-20 |
| IL166254A0 (en) | 2006-01-15 |
| US20050245567A1 (en) | 2005-11-03 |
| JP2005538187A (ja) | 2005-12-15 |
| EP1532144A1 (en) | 2005-05-25 |
| AU2003250322B2 (en) | 2010-01-21 |
| DE60318860D1 (de) | 2008-03-13 |
| BR0313153A (pt) | 2005-06-28 |
| US20090005390A1 (en) | 2009-01-01 |
| CN1675205A (zh) | 2005-09-28 |
| IS7742A (is) | 2005-03-14 |
| EP1905771A2 (en) | 2008-04-02 |
| AU2003250322A1 (en) | 2004-03-03 |
| PL375533A1 (en) | 2005-11-28 |
| CA2493245A1 (en) | 2004-02-26 |
| HK1080860A1 (zh) | 2006-05-04 |
| KR20050055711A (ko) | 2005-06-13 |
| ATE384720T1 (de) | 2008-02-15 |
| NO20051264L (no) | 2005-05-18 |
| WO2004016608A1 (en) | 2004-02-26 |
| EP1905771A3 (en) | 2008-11-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PSEA | Patent sealed | ||
| RENW | Renewal (renewal fees accepted) | ||
| RENW | Renewal (renewal fees accepted) | ||
| LAPS | Patent lapsed |