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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- 125000006137 n-hexyl sulfonyl group Chemical group 0.000 description 1
- NCCHARWOCKOHIH-UHFFFAOYSA-N n-methylbenzamide Chemical compound CNC(=O)C1=CC=CC=C1 NCCHARWOCKOHIH-UHFFFAOYSA-N 0.000 description 1
- 125000006129 n-pentyl sulfonyl group Chemical group 0.000 description 1
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- 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 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 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
- 230000003389 potentiating effect Effects 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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- FJYBLMJHXRWDAQ-UHFFFAOYSA-N tert-butyl 2-(hydroxymethyl)morpholine-4-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCOC(CO)C1 FJYBLMJHXRWDAQ-UHFFFAOYSA-N 0.000 description 1
- QAZYGHLQQPTQAX-UHFFFAOYSA-N tert-butyl 2-hydroxybenzoate Chemical compound CC(C)(C)OC(=O)C1=CC=CC=C1O QAZYGHLQQPTQAX-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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- JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- 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)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Immunology (AREA)
- Rheumatology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (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 (fr) | 2002-07-08 | 2003-07-07 | Nouvelles spiropiperidines ou spiropyrrolidines tricycliques |
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 (fr) |
| EP (1) | EP1521757B1 (fr) |
| JP (1) | JP2005537255A (fr) |
| CN (2) | CN1326858C (fr) |
| AR (1) | AR040475A1 (fr) |
| AT (1) | ATE385235T1 (fr) |
| AU (1) | AU2003243122B2 (fr) |
| BR (1) | BR0312560A (fr) |
| CA (1) | CA2492122A1 (fr) |
| CY (1) | CY1107915T1 (fr) |
| DE (1) | DE60318948T2 (fr) |
| DK (1) | DK1521757T3 (fr) |
| ES (1) | ES2298575T3 (fr) |
| HK (1) | HK1074622A1 (fr) |
| IS (1) | IS7662A (fr) |
| MX (1) | MXPA05000278A (fr) |
| NO (1) | NO20050635L (fr) |
| NZ (1) | NZ537259A (fr) |
| PL (1) | PL374877A1 (fr) |
| PT (1) | PT1521757E (fr) |
| RU (1) | RU2320664C2 (fr) |
| SE (1) | SE0202133D0 (fr) |
| TW (1) | TW200413386A (fr) |
| UA (1) | UA77809C2 (fr) |
| WO (1) | WO2004005295A1 (fr) |
| ZA (1) | ZA200500024B (fr) |
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 |
| US7732442B2 (en) | 2003-09-05 | 2010-06-08 | Ono Pharmaceutical Co., Ltd. | Chemokine receptor antagonist and medical use thereof |
| 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 |
| NZ551603A (en) | 2004-06-24 | 2010-11-26 | Incyte Corp | N-substituted piperidines and their use as pharmaceuticals |
| US20080306054A1 (en) | 2005-04-13 | 2008-12-11 | Astex Therapeutics Limited | Pharmaceutical Compounds |
| JP2009507800A (ja) | 2005-09-09 | 2009-02-26 | ユーロ−セルティーク エス．エイ． | 縮合およびスピロ環化合物ならびにその使用 |
| 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 |
| CA2657639A1 (fr) * | 2006-07-19 | 2008-01-24 | Astrazeneca Ab | Nouveaux composes |
| GB0620259D0 (en) | 2006-10-12 | 2006-11-22 | Astex Therapeutics Ltd | Pharmaceutical compounds |
| 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 |
| WO2008044029A1 (fr) | 2006-10-12 | 2008-04-17 | Astex Therapeutics Limited | Combinaisons pharmaceutiques |
| WO2008044054A2 (fr) | 2006-10-12 | 2008-04-17 | Astex Therapeutics Limited | Composés pharmaceutiques |
| EP2081891A2 (fr) | 2006-10-12 | 2009-07-29 | Astex Therapeutics Limited | COMPOSES PHARMACEUTIQUES AYANT UNE ACTIVITE INHIBITRICE OU MODULATRICE HSP90& xA; |
| 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 |
| JP5650404B2 (ja) | 2006-12-28 | 2015-01-07 | ライジェル ファーマシューティカルズ， インコーポレイテッド | Ｎ−置換−ヘテロシクロアルキルオキシベンズアミド化合物およびその使用方法 |
| WO2008103125A1 (fr) * | 2007-02-23 | 2008-08-28 | Astrazeneca Ab | Nouvelle combinaison de composés utilisés dans le traitement des maladies des voies aériennes, en particulier la bronchopneumopathie chronique obstructive (copd) et l'asthme |
| EP2120935A4 (fr) * | 2007-02-23 | 2011-06-22 | Astrazeneca Ab | Nouvelle combinaison de composés utilisés dans le traitement des maladies des voies aériennes, en particulier la bronchopneumopathie chronique obstructive (copd) et l'asthme |
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-
2002
- 2002-07-08 SE SE0202133A patent/SE0202133D0/xx unknown
-
2003
- 2003-07-03 TW TW092118200A patent/TW200413386A/zh unknown
- 2003-07-07 ES ES03762957T patent/ES2298575T3/es not_active Expired - Lifetime
- 2003-07-07 UA UA20041210166A patent/UA77809C2/uk unknown
- 2003-07-07 CN CNB038191466A patent/CN1326858C/zh not_active Expired - Fee Related
- 2003-07-07 CA CA002492122A patent/CA2492122A1/fr not_active Abandoned
- 2003-07-07 NZ NZ537259A patent/NZ537259A/en unknown
- 2003-07-07 US US10/520,699 patent/US7449475B2/en not_active Expired - Fee Related
- 2003-07-07 BR BR0312560-2A patent/BR0312560A/pt not_active IP Right Cessation
- 2003-07-07 DK DK03762957T patent/DK1521757T3/da active
- 2003-07-07 MX MXPA05000278A patent/MXPA05000278A/es active IP Right Grant
- 2003-07-07 PT PT03762957T patent/PT1521757E/pt unknown
- 2003-07-07 AT AT03762957T patent/ATE385235T1/de not_active IP Right Cessation
- 2003-07-07 CN CNA2006101435561A patent/CN1974574A/zh active Pending
- 2003-07-07 EP EP03762957A patent/EP1521757B1/fr not_active Expired - Lifetime
- 2003-07-07 AU AU2003243122A patent/AU2003243122B2/en not_active Ceased
- 2003-07-07 JP JP2004519472A patent/JP2005537255A/ja active Pending
- 2003-07-07 PL PL03374877A patent/PL374877A1/xx not_active Application Discontinuation
- 2003-07-07 DE DE60318948T patent/DE60318948T2/de not_active Expired - Fee Related
- 2003-07-07 RU RU2004137278/04A patent/RU2320664C2/ru not_active IP Right Cessation
- 2003-07-07 WO PCT/SE2003/001185 patent/WO2004005295A1/fr active IP Right Grant
- 2003-07-08 AR AR20030102463A patent/AR040475A1/es not_active Application Discontinuation
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2005
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- 2005-01-24 IS IS7662A patent/IS7662A/is unknown
- 2005-02-04 NO NO20050635A patent/NO20050635L/no not_active Application Discontinuation
- 2005-08-09 HK HK05106846A patent/HK1074622A1/xx not_active IP Right Cessation
-
2008
- 2008-04-03 CY CY20081100375T patent/CY1107915T1/el unknown
- 2008-11-05 US US12/265,251 patent/US20090062322A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| JP2005537255A (ja) | 2005-12-08 |
| NO20050635L (no) | 2005-03-31 |
| TW200413386A (en) | 2004-08-01 |
| US7449475B2 (en) | 2008-11-11 |
| CA2492122A1 (fr) | 2004-01-15 |
| ATE385235T1 (de) | 2008-02-15 |
| CY1107915T1 (el) | 2013-09-04 |
| ZA200500024B (en) | 2006-02-22 |
| CN1974574A (zh) | 2007-06-06 |
| SE0202133D0 (sv) | 2002-07-08 |
| NZ537259A (en) | 2006-08-31 |
| WO2004005295A1 (fr) | 2004-01-15 |
| AU2003243122A1 (en) | 2004-01-23 |
| EP1521757A1 (fr) | 2005-04-13 |
| DE60318948T2 (de) | 2009-05-20 |
| AU2003243122B2 (en) | 2006-09-28 |
| EP1521757B1 (fr) | 2008-01-30 |
| DE60318948D1 (de) | 2008-03-20 |
| CN1675218A (zh) | 2005-09-28 |
| IS7662A (is) | 2005-01-24 |
| US20090062322A1 (en) | 2009-03-05 |
| BR0312560A (pt) | 2005-05-10 |
| MXPA05000278A (es) | 2005-03-31 |
| PT1521757E (pt) | 2008-04-03 |
| DK1521757T3 (da) | 2008-05-05 |
| AR040475A1 (es) | 2005-04-06 |
| PL374877A1 (en) | 2005-11-14 |
| RU2320664C2 (ru) | 2008-03-27 |
| CN1326858C (zh) | 2007-07-18 |
| RU2004137278A (ru) | 2005-09-10 |
| US20050245741A1 (en) | 2005-11-03 |
| HK1074622A1 (en) | 2005-11-18 |
| ES2298575T3 (es) | 2008-05-16 |
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