UA77809C2 - Tricyclic spiropiperidines or spiropyrrolidines, method for their synthesis (variants), use thereof, method for treating inflammations and respiratory diseases, pharmaceutical composition, intermediate, method for producing intermediate - Google Patents
Tricyclic spiropiperidines or spiropyrrolidines, method for their synthesis (variants), use thereof, method for treating inflammations and respiratory diseases, pharmaceutical composition, intermediate, method for producing intermediate Download PDFInfo
- Publication number
- UA77809C2 UA77809C2 UA20041210166A UA20041210166A UA77809C2 UA 77809 C2 UA77809 C2 UA 77809C2 UA 20041210166 A UA20041210166 A UA 20041210166A UA 20041210166 A UA20041210166 A UA 20041210166A UA 77809 C2 UA77809 C2 UA 77809C2
- Authority
- UA
- Ukraine
- Prior art keywords
- spiro
- benzofuran
- chloro
- oxy
- hydroxypropyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 33
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 10
- 230000015572 biosynthetic process Effects 0.000 title claims description 19
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 206010061218 Inflammation Diseases 0.000 title 1
- 230000004054 inflammatory process Effects 0.000 title 1
- 208000023504 respiratory system disease Diseases 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 305
- 238000002560 therapeutic procedure Methods 0.000 claims abstract description 6
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- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 168
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 165
- -1 cyano, hydroxyl Chemical group 0.000 claims description 109
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 86
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 85
- 229910052757 nitrogen Inorganic materials 0.000 claims description 72
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 69
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 64
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 63
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 62
- 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 57
- JHHZLHWJQPUNKB-UHFFFAOYSA-N pyrrolidin-3-ol Chemical compound OC1CCNC1 JHHZLHWJQPUNKB-UHFFFAOYSA-N 0.000 claims description 55
- 125000001424 substituent group Chemical group 0.000 claims description 54
- 229910052736 halogen Inorganic materials 0.000 claims description 47
- 150000002367 halogens Chemical class 0.000 claims description 47
- 125000000623 heterocyclic group Chemical group 0.000 claims description 46
- 229920006395 saturated elastomer Polymers 0.000 claims description 43
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 39
- 229910052760 oxygen Inorganic materials 0.000 claims description 38
- 150000003839 salts Chemical class 0.000 claims description 38
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 37
- 239000001301 oxygen Chemical group 0.000 claims description 37
- 239000012453 solvate Substances 0.000 claims description 37
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 36
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- 125000005842 heteroatom Chemical group 0.000 claims description 34
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 33
- 229910052717 sulfur Chemical group 0.000 claims description 33
- 239000011593 sulfur Chemical group 0.000 claims description 33
- LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical compound NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 claims description 32
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- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 30
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- 229910052731 fluorine Inorganic materials 0.000 claims description 25
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- 239000002253 acid Substances 0.000 claims description 23
- 239000004202 carbamide Substances 0.000 claims description 23
- 239000000460 chlorine Substances 0.000 claims description 22
- 239000005711 Benzoic acid Substances 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 21
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 21
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 21
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- 125000004122 cyclic group Chemical group 0.000 claims description 18
- HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 claims description 18
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- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 16
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 15
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
- 125000004043 oxo group Chemical group O=* 0.000 claims description 13
- 201000010099 disease Diseases 0.000 claims description 11
- 125000006413 ring segment Chemical group 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
- 238000011282 treatment Methods 0.000 claims description 9
- BBWJIHMTJCJDKJ-UHFFFAOYSA-N 1,2-oxazolidin-4-ol Chemical compound OC1CNOC1 BBWJIHMTJCJDKJ-UHFFFAOYSA-N 0.000 claims description 8
- BIWOSRSKDCZIFM-UHFFFAOYSA-N piperidin-3-ol Chemical compound OC1CCCNC1 BIWOSRSKDCZIFM-UHFFFAOYSA-N 0.000 claims description 8
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims description 7
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- 229910052796 boron Inorganic materials 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- 125000001188 haloalkyl group Chemical group 0.000 claims description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 7
- QXSAKPUBHTZHKW-UHFFFAOYSA-N 4-hydroxybenzamide Chemical compound NC(=O)C1=CC=C(O)C=C1 QXSAKPUBHTZHKW-UHFFFAOYSA-N 0.000 claims description 6
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims description 6
- 208000006673 asthma Diseases 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 claims description 5
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000006239 protecting group Chemical group 0.000 claims description 5
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 5
- GKTFLKJXZOYBRW-UHFFFAOYSA-N 2-ethylbenzamide Chemical compound CCC1=CC=CC=C1C(N)=O GKTFLKJXZOYBRW-UHFFFAOYSA-N 0.000 claims description 4
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 4
- 239000002671 adjuvant Substances 0.000 claims description 4
- JXHYCCGOZUGBFD-UHFFFAOYSA-N benzoic acid;hydrochloride Chemical compound Cl.OC(=O)C1=CC=CC=C1 JXHYCCGOZUGBFD-UHFFFAOYSA-N 0.000 claims description 4
- 125000005059 halophenyl group Chemical group 0.000 claims description 4
- MTCFGRXMJLQNBG-UHFFFAOYSA-M serinate Chemical compound OCC(N)C([O-])=O MTCFGRXMJLQNBG-UHFFFAOYSA-M 0.000 claims description 4
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims description 4
- 102000009410 Chemokine receptor Human genes 0.000 claims description 3
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- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 3
- 230000000694 effects Effects 0.000 claims description 3
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 claims description 3
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 3
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- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- 201000006417 multiple sclerosis Diseases 0.000 claims description 2
- RSCLTAHCZHPGHS-UHFFFAOYSA-N pyrrolidin-3-yl benzoate Chemical compound C=1C=CC=CC=1C(=O)OC1CCNC1 RSCLTAHCZHPGHS-UHFFFAOYSA-N 0.000 claims description 2
- IQHXABCGSFAKPN-UHFFFAOYSA-N pyrrolidine-3-carboxamide Chemical compound NC(=O)C1CCNC1 IQHXABCGSFAKPN-UHFFFAOYSA-N 0.000 claims description 2
- 238000007363 ring formation reaction Methods 0.000 claims description 2
- 230000003993 interaction Effects 0.000 claims 5
- INTCGJHAECYOBW-APWZRJJASA-N (2s,3r)-4-(dimethylamino)-3-methyl-1,2-diphenylbutan-2-ol Chemical compound C([C@](O)([C@@H](CN(C)C)C)C=1C=CC=CC=1)C1=CC=CC=C1 INTCGJHAECYOBW-APWZRJJASA-N 0.000 claims 1
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- 150000004702 methyl esters Chemical class 0.000 description 1
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- 229910052700 potassium Inorganic materials 0.000 description 1
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Substances [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 1
- 235000007715 potassium iodide Nutrition 0.000 description 1
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- ZBYFQSPEUIVDTF-UHFFFAOYSA-N spiro[1,2-dihydroindene-3,4'-piperidine] Chemical compound C12=CC=CC=C2CCC21CCNCC2 ZBYFQSPEUIVDTF-UHFFFAOYSA-N 0.000 description 1
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- LTDRQRZCMHBRKM-UHFFFAOYSA-N tert-butyl 3-hydroxy-3-(trifluoromethyl)pyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(O)(C(F)(F)F)C1 LTDRQRZCMHBRKM-UHFFFAOYSA-N 0.000 description 1
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- 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
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- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/20—Spiro-condensed ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- 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
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- 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
-
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- 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
- 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
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pulmonology (AREA)
- Rheumatology (AREA)
- Immunology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0202133A SE0202133D0 (sv) | 2002-07-08 | 2002-07-08 | Novel compounds |
| PCT/SE2003/001185 WO2004005295A1 (en) | 2002-07-08 | 2003-07-07 | Novel tricyclic spiropiperidines or spiropyrrolidines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA77809C2 true UA77809C2 (en) | 2007-01-15 |
Family
ID=20288470
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA20041210166A UA77809C2 (en) | 2002-07-08 | 2003-07-07 | Tricyclic spiropiperidines or spiropyrrolidines, method for their synthesis (variants), use thereof, method for treating inflammations and respiratory diseases, pharmaceutical composition, intermediate, method for producing intermediate |
Country Status (26)
| Country | Link |
|---|---|
| US (2) | US7449475B2 (de) |
| EP (1) | EP1521757B1 (de) |
| JP (1) | JP2005537255A (de) |
| CN (2) | CN1326858C (de) |
| AR (1) | AR040475A1 (de) |
| AT (1) | ATE385235T1 (de) |
| AU (1) | AU2003243122B2 (de) |
| BR (1) | BR0312560A (de) |
| CA (1) | CA2492122A1 (de) |
| CY (1) | CY1107915T1 (de) |
| DE (1) | DE60318948T2 (de) |
| DK (1) | DK1521757T3 (de) |
| ES (1) | ES2298575T3 (de) |
| HK (1) | HK1074622A1 (de) |
| IS (1) | IS7662A (de) |
| MX (1) | MXPA05000278A (de) |
| NO (1) | NO20050635L (de) |
| NZ (1) | NZ537259A (de) |
| PL (1) | PL374877A1 (de) |
| PT (1) | PT1521757E (de) |
| RU (1) | RU2320664C2 (de) |
| SE (1) | SE0202133D0 (de) |
| TW (1) | TW200413386A (de) |
| UA (1) | UA77809C2 (de) |
| WO (1) | WO2004005295A1 (de) |
| ZA (1) | ZA200500024B (de) |
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE0202133D0 (sv) | 2002-07-08 | 2002-07-08 | Astrazeneca Ab | Novel compounds |
| EP1661889A4 (de) | 2003-09-05 | 2009-08-05 | Ono Pharmaceutical Co | Chemokinrezeptorantagonist und dessen medizinische verwendung |
| SE0302755D0 (sv) * | 2003-10-17 | 2003-10-17 | Astrazeneca Ab | Novel compounds |
| US20070021498A1 (en) * | 2004-10-14 | 2007-01-25 | Nafizal Hossain | Novel tricyclic spiroderivatives as modulators of chemokine receptor activity |
| SE0302811D0 (sv) * | 2003-10-23 | 2003-10-23 | Astrazeneca Ab | Novel compounds |
| SE0303090D0 (sv) * | 2003-11-20 | 2003-11-20 | Astrazeneca Ab | Novel compounds |
| SE0303280D0 (sv) * | 2003-12-05 | 2003-12-05 | Astrazeneca Ab | Novel compounds |
| SE0303541D0 (sv) | 2003-12-22 | 2003-12-22 | Astrazeneca Ab | New compounds |
| TWI350168B (en) | 2004-05-07 | 2011-10-11 | Incyte Corp | Amido compounds and their use as pharmaceuticals |
| US8071624B2 (en) | 2004-06-24 | 2011-12-06 | Incyte Corporation | N-substituted piperidines and their use as pharmaceuticals |
| DK1877379T3 (da) | 2005-04-13 | 2013-04-08 | Astex Therapeutics Ltd | Hydroxybenzamidderivater og anvendelse heraf som inhibitorer af hsp90 |
| WO2007028638A1 (en) | 2005-09-09 | 2007-03-15 | Euro-Celtique S.A. | Fused and spirocycle compounds and the use thereof |
| JP5315590B2 (ja) * | 2006-02-14 | 2013-10-16 | Ｊｎｃ株式会社 | 液晶化合物、液晶組成物および液晶表示素子 |
| US7754725B2 (en) | 2006-03-01 | 2010-07-13 | Astex Therapeutics Ltd. | Dihydroxyphenyl isoindolymethanones |
| CN101553493B (zh) * | 2006-07-19 | 2012-07-04 | 阿斯利康(瑞典)有限公司 | 三环螺哌啶化合物、它们的合成和它们作为趋化因子受体活性调节剂的用途 |
| JP5528807B2 (ja) | 2006-10-12 | 2014-06-25 | アステックス、セラピューティックス、リミテッド | 複合薬剤 |
| WO2008044029A1 (en) | 2006-10-12 | 2008-04-17 | Astex Therapeutics Limited | Pharmaceutical combinations |
| JP5518478B2 (ja) | 2006-10-12 | 2014-06-11 | アステックス、セラピューティックス、リミテッド | 医薬化合物 |
| JP5528806B2 (ja) | 2006-10-12 | 2014-06-25 | アステックス、セラピューティックス、リミテッド | 複合薬剤 |
| GB0620259D0 (en) | 2006-10-12 | 2006-11-22 | Astex Therapeutics Ltd | Pharmaceutical compounds |
| JP5410285B2 (ja) | 2006-10-12 | 2014-02-05 | アステックス、セラピューティックス、リミテッド | 医薬化合物 |
| CA2674237C (en) | 2006-12-28 | 2015-11-24 | Rigel Pharmaceuticals, Inc. | N-substituted-heterocycloalkyloxybenzamide compounds and methods of use |
| EP2125728A4 (de) * | 2007-02-23 | 2011-06-22 | Astrazeneca Ab | Neue kombination von verbindungen, die für die behandlung von atemwegserkrankungen, insbesondere chronisch-obstruktiver atemwegserkrankung (copd) und asthma, bestimmt ist |
| US20110124613A1 (en) * | 2007-02-23 | 2011-05-26 | Tomas Eriksson | Novel Combination of Compounds to be Used in the Treatment of Airway Diseases, Especially Chronic Obstructive Pulmonary Disease (COPD) and Asthma |
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-
2002
- 2002-07-08 SE SE0202133A patent/SE0202133D0/xx unknown
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2003
- 2003-07-03 TW TW092118200A patent/TW200413386A/zh unknown
- 2003-07-07 US US10/520,699 patent/US7449475B2/en not_active Expired - Fee Related
- 2003-07-07 CA CA002492122A patent/CA2492122A1/en not_active Abandoned
- 2003-07-07 CN CNB038191466A patent/CN1326858C/zh not_active Expired - Fee Related
- 2003-07-07 AT AT03762957T patent/ATE385235T1/de not_active IP Right Cessation
- 2003-07-07 RU RU2004137278/04A patent/RU2320664C2/ru not_active IP Right Cessation
- 2003-07-07 MX MXPA05000278A patent/MXPA05000278A/es active IP Right Grant
- 2003-07-07 DE DE60318948T patent/DE60318948T2/de not_active Expired - Fee Related
- 2003-07-07 ES ES03762957T patent/ES2298575T3/es not_active Expired - Lifetime
- 2003-07-07 DK DK03762957T patent/DK1521757T3/da active
- 2003-07-07 AU AU2003243122A patent/AU2003243122B2/en not_active Ceased
- 2003-07-07 WO PCT/SE2003/001185 patent/WO2004005295A1/en active IP Right Grant
- 2003-07-07 BR BR0312560-2A patent/BR0312560A/pt not_active IP Right Cessation
- 2003-07-07 EP EP03762957A patent/EP1521757B1/de not_active Expired - Lifetime
- 2003-07-07 JP JP2004519472A patent/JP2005537255A/ja active Pending
- 2003-07-07 UA UA20041210166A patent/UA77809C2/uk unknown
- 2003-07-07 NZ NZ537259A patent/NZ537259A/en unknown
- 2003-07-07 PT PT03762957T patent/PT1521757E/pt unknown
- 2003-07-07 CN CNA2006101435561A patent/CN1974574A/zh active Pending
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- 2003-07-08 AR AR20030102463A patent/AR040475A1/es not_active Application Discontinuation
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2005
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- 2005-08-09 HK HK05106846A patent/HK1074622A1/xx not_active IP Right Cessation
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2008
- 2008-04-03 CY CY20081100375T patent/CY1107915T1/el unknown
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Also Published As
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| EP1521757A1 (de) | 2005-04-13 |
| NZ537259A (en) | 2006-08-31 |
| HK1074622A1 (en) | 2005-11-18 |
| US20050245741A1 (en) | 2005-11-03 |
| DK1521757T3 (da) | 2008-05-05 |
| BR0312560A (pt) | 2005-05-10 |
| DE60318948D1 (de) | 2008-03-20 |
| NO20050635L (no) | 2005-03-31 |
| CN1326858C (zh) | 2007-07-18 |
| PT1521757E (pt) | 2008-04-03 |
| CA2492122A1 (en) | 2004-01-15 |
| RU2004137278A (ru) | 2005-09-10 |
| AU2003243122B2 (en) | 2006-09-28 |
| CY1107915T1 (el) | 2013-09-04 |
| JP2005537255A (ja) | 2005-12-08 |
| RU2320664C2 (ru) | 2008-03-27 |
| ES2298575T3 (es) | 2008-05-16 |
| PL374877A1 (en) | 2005-11-14 |
| CN1974574A (zh) | 2007-06-06 |
| EP1521757B1 (de) | 2008-01-30 |
| AU2003243122A1 (en) | 2004-01-23 |
| WO2004005295A1 (en) | 2004-01-15 |
| IS7662A (is) | 2005-01-24 |
| MXPA05000278A (es) | 2005-03-31 |
| CN1675218A (zh) | 2005-09-28 |
| SE0202133D0 (sv) | 2002-07-08 |
| ATE385235T1 (de) | 2008-02-15 |
| DE60318948T2 (de) | 2009-05-20 |
| AR040475A1 (es) | 2005-04-06 |
| ZA200500024B (en) | 2006-02-22 |
| TW200413386A (en) | 2004-08-01 |
| US20090062322A1 (en) | 2009-03-05 |
| US7449475B2 (en) | 2008-11-11 |
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