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 PDF

Info

Publication number: UA77809C2
Authority: UA; Ukraine
Prior art keywords: spiro; benzofuran; chloro; oxy; hydroxypropyl
Prior art date: 2002-07-08

Application number

UA20041210166A

Other languages

English (en)

Ukrainian (uk)

Original Assignee

Astrazeneca Ab

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2002-07-08

Filing date

2003-07-07

Publication date

2007-01-15

2003-07-07 Application filed by Astrazeneca Ab filed Critical Astrazeneca Ab

2007-01-15 Publication of UA77809C2 publication Critical patent/UA77809C2/uk

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
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 297
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
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 35
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
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 31
RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 30
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 29
229910052731 fluorine Inorganic materials 0.000 claims description 25
239000011737 fluorine Substances 0.000 claims description 24
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 23
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
229910052801 chlorine Inorganic materials 0.000 claims description 21
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
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 20
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 19
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
235000010233 benzoic acid Nutrition 0.000 claims description 17
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
229940090248 4-hydroxybenzoic acid Drugs 0.000 claims description 7
125000003368 amide group Chemical group 0.000 claims description 7
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
108050000299 Chemokine receptor Proteins 0.000 claims description 3
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
KGGHWIKBOIQEAJ-UHFFFAOYSA-N 2-fluorobenzamide Chemical compound NC(=O)C1=CC=CC=C1F KGGHWIKBOIQEAJ-UHFFFAOYSA-N 0.000 claims description 2
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
SKZKKFZAGNVIMN-UHFFFAOYSA-N Salicilamide Chemical compound NC(=O)C1=CC=CC=C1O SKZKKFZAGNVIMN-UHFFFAOYSA-N 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims description 2
239000010949 copper Substances 0.000 claims description 2
208000027866 inflammatory disease Diseases 0.000 claims description 2
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
KPGSFHSKMGACKM-UHFFFAOYSA-N 2-(2-methylpropyl)benzamide Chemical compound CC(C)CC1=CC=CC=C1C(N)=O KPGSFHSKMGACKM-UHFFFAOYSA-N 0.000 claims 1
UXGVMFHEKMGWMA-UHFFFAOYSA-N 2-benzofuran Chemical compound C1=CC=CC2=COC=C21 UXGVMFHEKMGWMA-UHFFFAOYSA-N 0.000 claims 1
235000002566 Capsicum Nutrition 0.000 claims 1
239000006002 Pepper Substances 0.000 claims 1
235000016761 Piper aduncum Nutrition 0.000 claims 1
235000017804 Piper guineense Nutrition 0.000 claims 1
244000203593 Piper nigrum Species 0.000 claims 1
235000008184 Piper nigrum Nutrition 0.000 claims 1
208000018569 Respiratory Tract disease Diseases 0.000 claims 1
230000009286 beneficial effect Effects 0.000 claims 1
WPYMKLBDIGXBTP-UHFFFAOYSA-M benzoate Chemical compound [O-]C(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-M 0.000 claims 1
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235000010290 biphenyl Nutrition 0.000 claims 1
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OJEYDZBIAYMFFD-UHFFFAOYSA-N cyclopentanecarboxamide Chemical compound NC(=O)C1C[CH]CC1 OJEYDZBIAYMFFD-UHFFFAOYSA-N 0.000 claims 1
125000004050 enoyl group Chemical group 0.000 claims 1
ALBYIUDWACNRRB-UHFFFAOYSA-N hexanamide Chemical compound CCCCCC(N)=O ALBYIUDWACNRRB-UHFFFAOYSA-N 0.000 claims 1
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238000012876 topography Methods 0.000 claims 1
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238000003818 flash chromatography Methods 0.000 description 124
235000019439 ethyl acetate Nutrition 0.000 description 117
238000005481 NMR spectroscopy Methods 0.000 description 113
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235000011152 sodium sulphate Nutrition 0.000 description 92
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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
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KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 1
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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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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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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

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Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Public Health (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)
Veterinary Medicine (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Pulmonology (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Immunology (AREA)
Rheumatology (AREA)
Physical Education & Sports Medicine (AREA)
Orthopedic Medicine & Surgery (AREA)
Psychiatry (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)
Hydrogenated Pyridines (AREA)
Plural Heterocyclic Compounds (AREA)
Other In-Based Heterocyclic Compounds (AREA)

UA20041210166A 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 UA77809C2 (en)

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

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Country Status (25)

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)
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)

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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 PL PL03374877A patent/PL374877A1/xx not_active Application Discontinuation
- 2003-07-07 ES ES03762957T patent/ES2298575T3/es not_active Expired - Lifetime
- 2003-07-07 DK DK03762957T patent/DK1521757T3/da active
- 2003-07-07 JP JP2004519472A patent/JP2005537255A/ja active Pending
- 2003-07-07 CN CNB038191466A patent/CN1326858C/zh not_active Expired - Fee Related
- 2003-07-07 EP EP03762957A patent/EP1521757B1/de not_active Expired - Lifetime
- 2003-07-07 CA CA002492122A patent/CA2492122A1/en not_active Abandoned
- 2003-07-07 WO PCT/SE2003/001185 patent/WO2004005295A1/en not_active Ceased
- 2003-07-07 BR BR0312560-2A patent/BR0312560A/pt not_active IP Right Cessation
- 2003-07-07 PT PT03762957T patent/PT1521757E/pt unknown
- 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 CN CNA2006101435561A patent/CN1974574A/zh active Pending
- 2003-07-07 RU RU2004137278/04A patent/RU2320664C2/ru not_active IP Right Cessation
- 2003-07-07 DE DE60318948T patent/DE60318948T2/de not_active Expired - Fee Related
- 2003-07-07 AU AU2003243122A patent/AU2003243122B2/en not_active Ceased
- 2003-07-07 UA UA20041210166A patent/UA77809C2/uk unknown
- 2003-07-07 AT AT03762957T patent/ATE385235T1/de not_active IP Right Cessation
- 2003-07-07 MX MXPA05000278A patent/MXPA05000278A/es active IP Right Grant
- 2003-07-08 AR AR20030102463A patent/AR040475A1/es not_active Application Discontinuation
2005
- 2005-01-03 ZA ZA200500024A patent/ZA200500024B/xx unknown
- 2005-01-24 IS IS7662A patent/IS7662A/is unknown
- 2005-02-04 NO NO20050635A patent/NO20050635L/no not_active Application Discontinuation
2008
- 2008-04-03 CY CY20081100375T patent/CY1107915T1/el unknown
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Also Published As

Publication number	Publication date
MXPA05000278A (es)	2005-03-31
ES2298575T3 (es)	2008-05-16
NZ537259A (en)	2006-08-31
US7449475B2 (en)	2008-11-11
ZA200500024B (en)	2006-02-22
DE60318948T2 (de)	2009-05-20
PL374877A1 (en)	2005-11-14
EP1521757B1 (de)	2008-01-30
AU2003243122A1 (en)	2004-01-23
WO2004005295A1 (en)	2004-01-15
DK1521757T3 (da)	2008-05-05
CN1675218A (zh)	2005-09-28
HK1074622A1 (en)	2005-11-18
CY1107915T1 (el)	2013-09-04
JP2005537255A (ja)	2005-12-08
RU2004137278A (ru)	2005-09-10
NO20050635L (no)	2005-03-31
US20050245741A1 (en)	2005-11-03
US20090062322A1 (en)	2009-03-05
AU2003243122B2 (en)	2006-09-28
IS7662A (is)	2005-01-24
RU2320664C2 (ru)	2008-03-27
CA2492122A1 (en)	2004-01-15
BR0312560A (pt)	2005-05-10
TW200413386A (en)	2004-08-01
AR040475A1 (es)	2005-04-06
DE60318948D1 (de)	2008-03-20
PT1521757E (pt)	2008-04-03
EP1521757A1 (de)	2005-04-13
SE0202133D0 (sv)	2002-07-08
CN1326858C (zh)	2007-07-18
ATE385235T1 (de)	2008-02-15
CN1974574A (zh)	2007-06-06

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