NZ528296A - Novel amides, preparation and therapeutic use as modulators of CCR-receptor activity - Google Patents
Novel amides, preparation and therapeutic use as modulators of CCR-receptor activityInfo
- Publication number
- NZ528296A NZ528296A NZ528296A NZ52829602A NZ528296A NZ 528296 A NZ528296 A NZ 528296A NZ 528296 A NZ528296 A NZ 528296A NZ 52829602 A NZ52829602 A NZ 52829602A NZ 528296 A NZ528296 A NZ 528296A
- Authority
- NZ
- New Zealand
- Prior art keywords
- compound
- formula
- group
- oxy
- pyridinyl
- Prior art date
Links
- 230000000694 effects Effects 0.000 title claims abstract description 9
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- 230000001225 therapeutic effect Effects 0.000 title description 4
- 150000001408 amides Chemical class 0.000 title description 2
- 102000005674 CCR Receptors Human genes 0.000 title 1
- 108010059983 CCR Receptors Proteins 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 83
- 238000000034 method Methods 0.000 claims abstract description 20
- 239000003814 drug Substances 0.000 claims abstract description 18
- 238000004519 manufacturing process Methods 0.000 claims abstract description 17
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 16
- 201000010099 disease Diseases 0.000 claims abstract description 14
- 208000006673 asthma Diseases 0.000 claims abstract description 8
- 238000011282 treatment Methods 0.000 claims abstract description 6
- 102000009410 Chemokine receptor Human genes 0.000 claims abstract description 5
- 108050000299 Chemokine receptor Proteins 0.000 claims abstract description 5
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims abstract description 5
- 206010039073 rheumatoid arthritis Diseases 0.000 claims abstract description 5
- 208000027866 inflammatory disease Diseases 0.000 claims abstract description 4
- 201000006417 multiple sclerosis Diseases 0.000 claims abstract description 4
- 230000009286 beneficial effect Effects 0.000 claims abstract description 3
- -1 nitro, carboxyl Chemical group 0.000 claims description 63
- 125000000217 alkyl group Chemical group 0.000 claims description 51
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 44
- 229910052757 nitrogen Inorganic materials 0.000 claims description 43
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 35
- 125000001424 substituent group Chemical group 0.000 claims description 33
- 150000003839 salts Chemical class 0.000 claims description 32
- 239000012453 solvate Substances 0.000 claims description 31
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 25
- 125000005842 heteroatom Chemical group 0.000 claims description 25
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 25
- 229920006395 saturated elastomer Polymers 0.000 claims description 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 23
- 229910052760 oxygen Inorganic materials 0.000 claims description 23
- 239000001301 oxygen Chemical group 0.000 claims description 23
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 22
- 229910052736 halogen Inorganic materials 0.000 claims description 22
- 150000002367 halogens Chemical class 0.000 claims description 22
- 125000000623 heterocyclic group Chemical group 0.000 claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 18
- 239000005864 Sulphur Chemical group 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 11
- 125000004414 alkyl thio group Chemical group 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 125000004122 cyclic group Chemical group 0.000 claims description 7
- 235000019256 formaldehyde Nutrition 0.000 claims description 7
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 6
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 6
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 6
- 230000035605 chemotaxis Effects 0.000 claims description 6
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 6
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- 239000002671 adjuvant Substances 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 125000001188 haloalkyl group Chemical group 0.000 claims description 5
- 125000004043 oxo group Chemical group O=* 0.000 claims description 5
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 4
- HJCMDXDYPOUFDY-WHFBIAKZSA-N Ala-Gln Chemical compound C[C@H](N)C(=O)N[C@H](C(O)=O)CCC(N)=O HJCMDXDYPOUFDY-WHFBIAKZSA-N 0.000 claims description 4
- 230000003213 activating effect Effects 0.000 claims description 4
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- GTKIGDZXPDCIKR-UHFFFAOYSA-N 2-phenylbenzamide Chemical compound NC(=O)C1=CC=CC=C1C1=CC=CC=C1 GTKIGDZXPDCIKR-UHFFFAOYSA-N 0.000 claims description 3
- 239000006146 Roswell Park Memorial Institute medium Substances 0.000 claims description 3
- 229910006074 SO2NH2 Inorganic materials 0.000 claims description 3
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 3
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- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
- 239000012737 fresh medium Substances 0.000 claims description 2
- 239000002609 medium Substances 0.000 claims description 2
- SADOZWPEQLXMES-UHFFFAOYSA-N n-[2-[3-[3-(5-chloropyridin-2-yl)oxypyrrolidin-1-yl]-2-hydroxypropoxy]phenyl]benzamide Chemical compound C1CC(OC=2N=CC(Cl)=CC=2)CN1CC(O)COC1=CC=CC=C1NC(=O)C1=CC=CC=C1 SADOZWPEQLXMES-UHFFFAOYSA-N 0.000 claims description 2
- OQBQUHFEASWWII-ZENAZSQFSA-N n-[4-fluoro-2-[(2s)-2-hydroxy-3-[3-(4-methylpyridin-2-yl)oxypyrrolidin-1-yl]propoxy]phenyl]acetamide Chemical compound CC(=O)NC1=CC=C(F)C=C1OC[C@@H](O)CN1CC(OC=2N=CC=C(C)C=2)CC1 OQBQUHFEASWWII-ZENAZSQFSA-N 0.000 claims description 2
- 239000005557 antagonist Substances 0.000 claims 4
- BQRGNLJZBFXNCZ-UHFFFAOYSA-N calcein am Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC(CN(CC(=O)OCOC(C)=O)CC(=O)OCOC(C)=O)=C(OC(C)=O)C=C1OC1=C2C=C(CN(CC(=O)OCOC(C)=O)CC(=O)OCOC(=O)C)C(OC(C)=O)=C1 BQRGNLJZBFXNCZ-UHFFFAOYSA-N 0.000 claims 2
- 238000005119 centrifugation Methods 0.000 claims 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- GYRPBSJQUIPFNP-UHFFFAOYSA-N N-[2-[3-[3-(5-chloropyridin-2-yl)oxypyrrolidin-1-yl]-2-hydroxypropoxy]phenyl]-2-(3,5-dimethyl-1H-pyrrol-2-yl)acetamide Chemical compound ClC=1C=CC(=NC=1)OC1CN(CC1)CC(COC1=C(C=CC=C1)NC(=O)CC=1NC(=CC=1C)C)O GYRPBSJQUIPFNP-UHFFFAOYSA-N 0.000 claims 1
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- 238000013508 migration Methods 0.000 claims 1
- PLOLENUQLVJTDI-UHFFFAOYSA-N n-[2-[3-[3-(5-bromopyridin-2-yl)oxypyrrolidin-1-yl]-2-hydroxypropoxy]-6-fluorophenyl]acetamide Chemical compound CC(=O)NC1=C(F)C=CC=C1OCC(O)CN1CC(OC=2N=CC(Br)=CC=2)CC1 PLOLENUQLVJTDI-UHFFFAOYSA-N 0.000 claims 1
- KXMCIJXWCHEMKS-UHFFFAOYSA-N n-[2-[3-[3-(5-bromopyridin-2-yl)oxypyrrolidin-1-yl]-2-hydroxypropoxy]phenyl]benzamide Chemical compound C1CC(OC=2N=CC(Br)=CC=2)CN1CC(O)COC1=CC=CC=C1NC(=O)C1=CC=CC=C1 KXMCIJXWCHEMKS-UHFFFAOYSA-N 0.000 claims 1
- XYYDZEHECXREQE-UHFFFAOYSA-N n-[2-[3-[3-(5-chloropyridin-2-yl)oxypyrrolidin-1-yl]-2-hydroxypropoxy]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC=C1OCC(O)CN1CC(OC=2N=CC(Cl)=CC=2)CC1 XYYDZEHECXREQE-UHFFFAOYSA-N 0.000 claims 1
- NOKSELYQYYLEGW-UHFFFAOYSA-N n-[2-[3-[3-(6-chloropyridin-2-yl)oxypyrrolidin-1-yl]-2-hydroxypropoxy]phenyl]benzamide Chemical compound C1CC(OC=2N=C(Cl)C=CC=2)CN1CC(O)COC1=CC=CC=C1NC(=O)C1=CC=CC=C1 NOKSELYQYYLEGW-UHFFFAOYSA-N 0.000 claims 1
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- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pulmonology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Rheumatology (AREA)
- Psychiatry (AREA)
- Physical Education & Sports Medicine (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Peptides Or Proteins (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0101038A SE0101038D0 (sv) | 2001-03-23 | 2001-03-23 | Novel compounds |
| PCT/SE2002/000541 WO2002076457A1 (en) | 2001-03-23 | 2002-03-19 | Novel amides, preparation and therapeutic use as modulators of ccr-receptor activity |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ528296A true NZ528296A (en) | 2005-03-24 |
Family
ID=20283509
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ528296A NZ528296A (en) | 2001-03-23 | 2002-03-19 | Novel amides, preparation and therapeutic use as modulators of CCR-receptor activity |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US7345063B2 (enExample) |
| EP (1) | EP1372651B1 (enExample) |
| JP (1) | JP2004524345A (enExample) |
| KR (1) | KR20030085030A (enExample) |
| CN (1) | CN1538844A (enExample) |
| AT (1) | ATE355842T1 (enExample) |
| BR (1) | BR0208336A (enExample) |
| CA (1) | CA2441933A1 (enExample) |
| DE (1) | DE60218641T2 (enExample) |
| DK (1) | DK1372651T3 (enExample) |
| ES (1) | ES2280511T3 (enExample) |
| IL (1) | IL157653A0 (enExample) |
| MX (1) | MXPA03008443A (enExample) |
| NO (1) | NO20034215L (enExample) |
| NZ (1) | NZ528296A (enExample) |
| PT (1) | PT1372651E (enExample) |
| SE (1) | SE0101038D0 (enExample) |
| SI (1) | SI1372651T1 (enExample) |
| WO (1) | WO2002076457A1 (enExample) |
| ZA (1) | ZA200306792B (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CO5300399A1 (es) | 2000-02-25 | 2003-07-31 | Astrazeneca Ab | Heterocicliocs que contienen nitrogeno, proceso para su preparacion y composiciones farmaceuticas que los contienen |
| US7005439B2 (en) * | 2000-06-20 | 2006-02-28 | Astrazeneca Ab | Compounds |
| AR028948A1 (es) * | 2000-06-20 | 2003-05-28 | Astrazeneca Ab | Compuestos novedosos |
| EP1661889A4 (en) * | 2003-09-05 | 2009-08-05 | Ono Pharmaceutical Co | ANTAGONIST OF THE CHEMOKINE RECEPTOR AND ITS USE FOR MEDICAL PURPOSES |
| EP1899322B1 (en) | 2005-06-28 | 2009-09-02 | Sanofi-Aventis | Isoquinoline derivatives as inhibitors of rho-kinase |
| HRP20110839T1 (hr) | 2005-07-26 | 2011-12-31 | Sanofi | Derivati cikloheksaminizokinolona kao inhibitori rho-kinaze |
| PT1910333E (pt) | 2005-07-26 | 2013-08-01 | Sanofi Sa | Derivados de isoquinolona substituída com piperidinilo como inibidores da rho-cinase |
| TW200738634A (en) * | 2005-08-02 | 2007-10-16 | Astrazeneca Ab | New salt |
| CN101595094B (zh) | 2006-12-27 | 2013-02-20 | 塞诺菲-安万特股份有限公司 | 环烷基胺取代的异喹诺酮衍生物 |
| EP2102164B1 (en) | 2006-12-27 | 2010-12-01 | Sanofi-Aventis | Cycloalkylamine substituted isoquinoline and isoquinolinone derivatives |
| ATE502027T1 (de) | 2006-12-27 | 2011-04-15 | Sanofi Aventis | Substituierte isochinoline und ihre verwendung als rho-kinase-inhibitoren |
| AU2007338410B2 (en) | 2006-12-27 | 2012-08-16 | Sanofi-Aventis | Cycloalkylamine substituted isoquinoline derivatives |
| JP5421783B2 (ja) | 2006-12-27 | 2014-02-19 | サノフイ | Ｒｈｏキナーゼ阻害剤としての置換イソキノロン及びイソキノリノン誘導体 |
| KR20090094338A (ko) | 2006-12-27 | 2009-09-04 | 사노피-아벤티스 | 치환된 이소퀴놀린 및 이소퀴놀리논 유도체 |
| SI2303845T1 (sl) | 2008-06-24 | 2013-12-31 | Sanofi | Bi- in policiklični substituirani izokinolin in izokinolinski derivati kot inhibitorji rho-kinaze |
| PE20110059A1 (es) | 2008-06-24 | 2011-02-15 | Sanofi Aventis | Isoquinolinas e isoquinolinonas sustituidas en calidad de inhibidores de la rho-quinasa |
| PL2313374T3 (pl) | 2008-06-24 | 2014-03-31 | Sanofi Sa | 6-podstawione izochinoliny i izochinolinony |
Family Cites Families (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1220440B (de) | 1962-02-14 | 1966-07-07 | Sanol Arznei Schwarz Gmbh | Verfahren zur Herstellung von Derivaten des 1-(o-Bromphenoxy)-2-hydroxy-3-amino-propans und deren Saeureadditionssalzen |
| US3577432A (en) | 1968-12-23 | 1971-05-04 | Robins Co Inc A H | 1-substituted-3-phenoxypyrrolidines |
| US4029801A (en) | 1970-09-03 | 1977-06-14 | John Wyeth & Brother Limited | Pharmaceutical compositions and methods of treating hypertension |
| JPS5511670B1 (enExample) | 1971-07-13 | 1980-03-26 | ||
| US4080328A (en) | 1971-07-13 | 1978-03-21 | Sumitomo Chemical Company, Limited | N-substituted heterocyclic derivatives and preparation thereof |
| US3755584A (en) | 1972-04-03 | 1973-08-28 | Abbott Lab | Tranquilizers |
| FR2190430A1 (en) | 1972-06-29 | 1974-02-01 | Ferlux | N-aminomethylhydroxamic acids - with antiinflammatory activity pre-pared by Mannich reaction |
| US3818017A (en) | 1973-01-04 | 1974-06-18 | Janssen Pharmaceutica Nv | 1-{8 1-(2-hydroxy-3-aryloxypropyl)-4-piperidyl{9 -2-benzimidazolinones and related compounds |
| US3894030A (en) | 1973-01-04 | 1975-07-08 | Janssen Pharmaceutica Nv | 1-{8 1-(2-Hydroxy-3-aryloxypropyl)-4-piperidyl{9 -2-benzimidazolinones and related compounds |
| US4166119A (en) | 1978-04-14 | 1979-08-28 | American Hoechst Corporation | Analgesic and tranquilizing spiro[dihydrobenzofuran]piperidines and pyrrolidines |
| WO1980000152A1 (fr) | 1978-07-03 | 1980-02-07 | Sandoz Ag | Derives d'un 3-aminopropoxy-aryle, leur preparation et utilisation |
| US4264613A (en) | 1979-08-01 | 1981-04-28 | Science Union Et Cie, Societe Francaise De Recherche Medicale | Piperidylbenzimidazolinone compounds |
| FR2469411A1 (fr) | 1979-11-15 | 1981-05-22 | Science Union & Cie | Nouveaux derives de la piperidylbenzimidazolinone, leurs procedes de preparation et les compositions pharmaceutiques les renfermant |
| EP0095454A3 (de) | 1982-05-13 | 1985-04-03 | Gerot-Pharmazeutika Gesellschaft m.b.H. | Neue kernsubstituierte Pyrogallol-Derivate |
| JPS59222484A (ja) | 1983-06-02 | 1984-12-14 | Kowa Co | テトラヒドロナフチルカルボン酸フエニルエステル誘導体 |
| US5614533A (en) | 1987-03-13 | 1997-03-25 | Bio-Mega/Boehringer Ingelheim Research, Inc. | Substituted pipecolinic acid derivatives as HIV protease inhibitors |
| DE3723568C2 (de) | 1987-07-16 | 1994-01-27 | Siemens Ag | Differenzstromschutzschalter |
| DE3723648A1 (de) | 1987-07-17 | 1989-01-26 | Sandoz Ag | Indol-derivate, ihre herstellung und sie enthaltende arzneimittel |
| ES2027897A6 (es) | 1991-01-24 | 1992-06-16 | Espanola Prod Quimicos | Procedimiento de preparacion de nuevos derivados de la difenilmetilpiperacina. |
| IL105716A0 (en) | 1992-06-08 | 1993-09-22 | Richter Gedeon Vegyeszet | Aminopropanol derivatives,their preparation and pharmaceutical compositions containing them |
| NZ248332A (en) | 1992-08-07 | 1995-01-27 | Sankyo Co | Hiv protease inhibitor and its use |
| US5576321A (en) | 1995-01-17 | 1996-11-19 | Eli Lilly And Company | Compounds having effects on serotonin-related systems |
| US5627196A (en) | 1995-01-17 | 1997-05-06 | Eli Lilly And Company | Compounds having effects on serotonin-related systems |
| US5741789A (en) | 1995-01-17 | 1998-04-21 | Eli Lilly And Company | Compounds having effects on serotonin-related systems |
| US5614523A (en) | 1995-01-17 | 1997-03-25 | Eli Lilly And Company | Compounds having effects on serotonin-related systems |
| US5789402A (en) | 1995-01-17 | 1998-08-04 | Eli Lilly Company | Compounds having effects on serotonin-related systems |
| ZA9610738B (en) | 1995-12-22 | 1997-06-24 | Warner Lambert Co | Subtype selective nmda receptor ligands and the use thereof |
| DE19703131A1 (de) | 1997-01-29 | 1998-07-30 | Bayer Ag | Verwendung von Chinoxalin in Dreier-Kombination mit Protease-Inhibitoren und Reverse Transkriptaseinhibitoren als Arzneimittel zur Behandlung von AIDS und/oder HIV-Infektionen |
| IL125658A0 (en) | 1997-08-18 | 1999-04-11 | Hoffmann La Roche | Ccr-3 receptor antagonists |
| HUP0004200A3 (en) | 1997-11-18 | 2001-04-28 | Dupont Pharmaceuticals Res Lab | Cyclic amine derivatives and their use as drugs |
| DE19755268A1 (de) | 1997-12-12 | 1999-06-17 | Merck Patent Gmbh | Benzamidinderivate |
| FR2780057B1 (fr) * | 1998-06-18 | 2002-09-13 | Sanofi Sa | Phenoxypropanolamines, procede pour leur preparation et compositions pharmaceutiques les contenant |
| AU2057200A (en) | 1998-12-18 | 2000-07-03 | Du Pont Pharmaceuticals Company | N-ureidoalkyl-piperidines as modulators of chemokine receptor activity |
| AU2482100A (en) | 1998-12-18 | 2000-07-03 | Du Pont Pharmaceuticals Company | N-ureidoalkyl-piperidines as modulators of chemokine receptor activity |
| AU2942000A (en) | 1999-03-11 | 2000-09-28 | Banyu Pharmaceutical Co., Ltd. | Novel piperidine derivatives |
| AU4157500A (en) | 1999-03-26 | 2000-10-16 | Astrazeneca Ab | Novel compounds |
| DE60014361T2 (de) | 1999-05-14 | 2006-02-02 | Bristol-Myers Squibb Pharma Research Labs, Inc. | Zyklische aminderivate und ihre verwendung |
| SE9902987D0 (sv) | 1999-08-24 | 1999-08-24 | Astra Pharma Prod | Novel compounds |
| AU2525801A (en) | 1999-12-17 | 2001-06-25 | Sanofi-Synthelabo | Phenoxypropanolamines, method for producing them and pharmaceutical compositionscontaining them |
| FR2802533B1 (fr) | 1999-12-17 | 2002-02-15 | Sanofi Synthelabo | Phenoxypropanolamines, leur preparation et leur application en therapeutique |
| CO5300399A1 (es) * | 2000-02-25 | 2003-07-31 | Astrazeneca Ab | Heterocicliocs que contienen nitrogeno, proceso para su preparacion y composiciones farmaceuticas que los contienen |
| GB0011838D0 (en) | 2000-05-17 | 2000-07-05 | Astrazeneca Ab | Chemical compounds |
-
2001
- 2001-03-23 SE SE0101038A patent/SE0101038D0/xx unknown
-
2002
- 2002-03-19 SI SI200230517T patent/SI1372651T1/sl unknown
- 2002-03-19 DE DE60218641T patent/DE60218641T2/de not_active Expired - Fee Related
- 2002-03-19 MX MXPA03008443A patent/MXPA03008443A/es active IP Right Grant
- 2002-03-19 CN CNA028070968A patent/CN1538844A/zh active Pending
- 2002-03-19 WO PCT/SE2002/000541 patent/WO2002076457A1/en not_active Ceased
- 2002-03-19 DK DK02708893T patent/DK1372651T3/da active
- 2002-03-19 ES ES02708893T patent/ES2280511T3/es not_active Expired - Lifetime
- 2002-03-19 BR BR0208336-1A patent/BR0208336A/pt not_active IP Right Cessation
- 2002-03-19 CA CA002441933A patent/CA2441933A1/en not_active Abandoned
- 2002-03-19 PT PT02708893T patent/PT1372651E/pt unknown
- 2002-03-19 JP JP2002574972A patent/JP2004524345A/ja active Pending
- 2002-03-19 AT AT02708893T patent/ATE355842T1/de not_active IP Right Cessation
- 2002-03-19 IL IL15765302A patent/IL157653A0/xx unknown
- 2002-03-19 NZ NZ528296A patent/NZ528296A/en unknown
- 2002-03-19 EP EP02708893A patent/EP1372651B1/en not_active Expired - Lifetime
- 2002-03-19 KR KR10-2003-7012302A patent/KR20030085030A/ko not_active Ceased
- 2002-03-19 US US10/472,017 patent/US7345063B2/en not_active Expired - Fee Related
-
2003
- 2003-08-29 ZA ZA200306792A patent/ZA200306792B/en unknown
- 2003-09-22 NO NO20034215A patent/NO20034215L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| KR20030085030A (ko) | 2003-11-01 |
| NO20034215D0 (no) | 2003-09-22 |
| CN1538844A (zh) | 2004-10-20 |
| DE60218641T2 (de) | 2007-11-29 |
| MXPA03008443A (es) | 2004-01-29 |
| US7345063B2 (en) | 2008-03-18 |
| CA2441933A1 (en) | 2002-10-03 |
| SI1372651T1 (sl) | 2007-06-30 |
| WO2002076457A1 (en) | 2002-10-03 |
| US20040122020A1 (en) | 2004-06-24 |
| ZA200306792B (en) | 2004-11-29 |
| SE0101038D0 (sv) | 2001-03-23 |
| DK1372651T3 (da) | 2007-05-29 |
| EP1372651B1 (en) | 2007-03-07 |
| JP2004524345A (ja) | 2004-08-12 |
| EP1372651A1 (en) | 2004-01-02 |
| PT1372651E (pt) | 2007-05-31 |
| ATE355842T1 (de) | 2007-03-15 |
| BR0208336A (pt) | 2004-03-23 |
| DE60218641D1 (de) | 2007-04-19 |
| IL157653A0 (en) | 2004-03-28 |
| ES2280511T3 (es) | 2007-09-16 |
| NO20034215L (no) | 2003-11-24 |
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Legal Events
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| PSEA | Patent sealed | ||
| RENW | Renewal (renewal fees accepted) |