ZA200604020B - Novel compounds - Google Patents
Novel compounds Download PDFInfo
- Publication number
- ZA200604020B ZA200604020B ZA200604020A ZA200604020A ZA200604020B ZA 200604020 B ZA200604020 B ZA 200604020B ZA 200604020 A ZA200604020 A ZA 200604020A ZA 200604020 A ZA200604020 A ZA 200604020A ZA 200604020 B ZA200604020 B ZA 200604020B
- Authority
- ZA
- South Africa
- Prior art keywords
- chloro
- benzofuran
- piperidin
- spiro
- propan
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 29
- -1 cyano, hydroxyl Chemical group 0.000 claims description 46
- 125000000217 alkyl group Chemical group 0.000 claims description 35
- 229910052736 halogen Inorganic materials 0.000 claims description 25
- 150000002367 halogens Chemical class 0.000 claims description 25
- 125000001424 substituent group Chemical group 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 125000000623 heterocyclic group Chemical group 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 15
- 239000012453 solvate Substances 0.000 claims description 13
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
- 125000001188 haloalkyl group Chemical group 0.000 claims description 11
- 125000005842 heteroatom Chemical group 0.000 claims description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- 229920006395 saturated elastomer Polymers 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 239000001301 oxygen Chemical group 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 239000005864 Sulphur Chemical group 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 5
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 5
- 125000002757 morpholinyl group Chemical group 0.000 claims description 5
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 5
- 125000003386 piperidinyl group Chemical group 0.000 claims description 5
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 2
- 208000006673 asthma Diseases 0.000 claims description 2
- 201000010099 disease Diseases 0.000 claims description 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 33
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 8
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 7
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims 5
- 239000003814 drug Substances 0.000 claims 5
- 238000004519 manufacturing process Methods 0.000 claims 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims 4
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims 3
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
- 239000002671 adjuvant Substances 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims 2
- VFTLWHYAPWDPPI-FQEVSTJZSA-N (2s)-1-(4-chloro-5-methyl-2-propan-2-ylphenoxy)-3-(5-chlorospiro[3h-1-benzofuran-2,4'-piperidine]-1'-yl)propan-2-ol Chemical compound CC(C)C1=CC(Cl)=C(C)C=C1OC[C@@H](O)CN1CCC2(OC3=CC=C(Cl)C=C3C2)CC1 VFTLWHYAPWDPPI-FQEVSTJZSA-N 0.000 claims 1
- UIHIUKFYVQAEEH-HNNXBMFYSA-N (2s)-1-(5-chlorospiro[3h-1-benzofuran-2,4'-piperidine]-1'-yl)-3-(2,3,6-trichlorophenoxy)propan-2-ol Chemical compound C([C@@H](O)CN1CCC2(OC3=CC=C(Cl)C=C3C2)CC1)OC1=C(Cl)C=CC(Cl)=C1Cl UIHIUKFYVQAEEH-HNNXBMFYSA-N 0.000 claims 1
- PIBQQFALUKSVHY-FQEVSTJZSA-N (2s)-1-(5-chlorospiro[3h-1-benzofuran-2,4'-piperidine]-1'-yl)-3-(3-ethylphenoxy)propan-2-ol Chemical compound CCC1=CC=CC(OC[C@@H](O)CN2CCC3(OC4=CC=C(Cl)C=C4C3)CC2)=C1 PIBQQFALUKSVHY-FQEVSTJZSA-N 0.000 claims 1
- DIIOHGGGTYCYOD-FYZYNONXSA-N (2s)-1-(5-chlorospiro[3h-1-benzofuran-2,4'-piperidine]-1'-yl)-3-[2-(2-hydroxyethoxy)phenoxy]propan-2-ol;hydrochloride Chemical compound Cl.OCCOC1=CC=CC=C1OC[C@@H](O)CN1CCC2(OC3=CC=C(Cl)C=C3C2)CC1 DIIOHGGGTYCYOD-FYZYNONXSA-N 0.000 claims 1
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- NYYZINHUDMCQLJ-KRWDZBQOSA-N 2-[(2s)-3-(5-chlorospiro[3h-1-benzofuran-2,4'-piperidine]-1'-yl)-2-hydroxypropoxy]phenol Chemical compound C([C@@H](O)CN1CCC2(OC3=CC=C(Cl)C=C3C2)CC1)OC1=CC=CC=C1O NYYZINHUDMCQLJ-KRWDZBQOSA-N 0.000 claims 1
- 239000001431 2-methylbenzaldehyde Substances 0.000 claims 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 1
- 101100409539 Caenorhabditis elegans pas-7 gene Proteins 0.000 claims 1
- 102000009410 Chemokine receptor Human genes 0.000 claims 1
- 108050000299 Chemokine receptor Proteins 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 230000009286 beneficial effect Effects 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- BPAWUEYRQUKRDC-XPUAEESYSA-N ethyl (E)-3-[4-[(2S)-3-(5-chlorospiro[3H-1-benzofuran-2,4'-piperidine]-1'-yl)-2-hydroxypropoxy]-3-methoxyphenyl]prop-2-enoate Chemical compound COC1=CC(/C=C/C(=O)OCC)=CC=C1OC[C@@H](O)CN1CCC2(OC3=CC=C(Cl)C=C3C2)CC1 BPAWUEYRQUKRDC-XPUAEESYSA-N 0.000 claims 1
- AKPUJVVHYUHGKY-UHFFFAOYSA-N hydron;propan-2-ol;chloride Chemical compound Cl.CC(C)O AKPUJVVHYUHGKY-UHFFFAOYSA-N 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 239000012948 isocyanate Substances 0.000 claims 1
- 150000002513 isocyanates Chemical class 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical compound CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 13
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- 229910052731 fluorine Inorganic materials 0.000 description 9
- 239000011737 fluorine Substances 0.000 description 9
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 9
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 9
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 9
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 9
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 8
- 229910052801 chlorine Inorganic materials 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
- 229910052794 bromium Inorganic materials 0.000 description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
- 229910052740 iodine Inorganic materials 0.000 description 5
- 239000011630 iodine Substances 0.000 description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 3
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- 108020003175 receptors Proteins 0.000 description 3
- OABOXRPGTFRBFZ-IMJSIDKUSA-N Cys-Cys Chemical compound SC[C@H](N)C(=O)N[C@@H](CS)C(O)=O OABOXRPGTFRBFZ-IMJSIDKUSA-N 0.000 description 2
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- 102100036154 Platelet basic protein Human genes 0.000 description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 2
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
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- XKTZWUACRZHVAN-VADRZIEHSA-N interleukin-8 Chemical compound C([C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@@H](NC(C)=O)CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CCSC)C(=O)N1[C@H](CCC1)C(=O)N1[C@H](CCC1)C(=O)N[C@@H](C)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC=1C=CC(O)=CC=1)C(=O)N[C@H](CO)C(=O)N1[C@H](CCC1)C(N)=O)C1=CC=CC=C1 XKTZWUACRZHVAN-VADRZIEHSA-N 0.000 description 2
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- 125000001298 n-hexoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 2
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- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
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- 125000006328 iso-butylcarbonyl group Chemical group [H]C([H])([H])C([H])(C(*)=O)C([H])([H])[H] 0.000 description 1
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- AEUKDPKXTPNBNY-XEYRWQBLSA-N mcp 2 Chemical compound C([C@@H](C(=O)N[C@@H](CS)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CCCNC(N)=N)C(=O)NCC(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CS)C(=O)N[C@@H](CS)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)NC(=O)CNC(=O)[C@H](C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC(C)C)NC(=O)[C@H](CS)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CS)NC(=O)[C@H](C)NC(=O)[C@H](CS)NC(=O)[C@@H](NC(=O)[C@@H](N)C(C)C)C(C)C)C1=CC=CC=C1 AEUKDPKXTPNBNY-XEYRWQBLSA-N 0.000 description 1
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- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
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- 125000003226 pyrazolyl group Chemical group 0.000 description 1
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- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 125000006253 t-butylcarbonyl group Chemical group [H]C([H])([H])C(C(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- 125000003831 tetrazolyl group Chemical group 0.000 description 1
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Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive 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
-
- 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
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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
- 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
- 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
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- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/10—Spiro-condensed systems
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- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Immunology (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0303090A SE0303090D0 (sv) | 2003-11-20 | 2003-11-20 | Novel compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200604020B true ZA200604020B (en) | 2007-12-27 |
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Family Applications (1)
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| ZA200604020A ZA200604020B (en) | 2003-11-20 | 2006-05-18 | Novel compounds |
Country Status (14)
| Country | Link |
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| US (1) | US7498338B2 (https=) |
| EP (1) | EP1687311A1 (https=) |
| JP (1) | JP2007512323A (https=) |
| KR (1) | KR20060111518A (https=) |
| CN (1) | CN1906200A (https=) |
| AU (1) | AU2004291455B2 (https=) |
| BR (1) | BRPI0416745A (https=) |
| CA (1) | CA2546028A1 (https=) |
| IL (1) | IL175437A0 (https=) |
| NO (1) | NO20062900L (https=) |
| NZ (1) | NZ547259A (https=) |
| SE (1) | SE0303090D0 (https=) |
| WO (1) | WO2005049620A1 (https=) |
| ZA (1) | ZA200604020B (https=) |
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| SE0202133D0 (sv) | 2002-07-08 | 2002-07-08 | Astrazeneca Ab | Novel compounds |
| SE0303090D0 (sv) | 2003-11-20 | 2003-11-20 | Astrazeneca Ab | Novel compounds |
| SE0303541D0 (sv) * | 2003-12-22 | 2003-12-22 | Astrazeneca Ab | New compounds |
| EP1981845A2 (en) * | 2006-02-08 | 2008-10-22 | Wyeth | Sulfonamide derivatives to treat infection with hepatitis c virus |
| BRPI0714463A2 (pt) * | 2006-07-19 | 2013-04-02 | Astrazeneca Ab | compostos de espiropiperidina tricÍclicos, sua sÍntese e seus usos como moduladores de atividade receptora de quimiocina |
| WO2008103126A1 (en) * | 2007-02-23 | 2008-08-28 | Astrazeneca Ab | Novel combination of compounds to be used in the treatment of airway diseases, especially chronic obstructive pulmonary disease (copd) and asthma |
| US20110136843A1 (en) * | 2007-02-23 | 2011-06-09 | Tomas Eriksson | Novel Combination of Compounds to be Used in the Treatment of Airway Diseases, Especially Chronic Obstructive Pulmonary Disease (COPD) and Asthma |
| WO2009011654A1 (en) * | 2007-07-17 | 2009-01-22 | Astrazeneca Ab | Process for the preparation of cyclic spiropiperidines |
| WO2009011655A1 (en) * | 2007-07-17 | 2009-01-22 | Astrazeneca Ab | Splropiperidine compounds, a process of their preparation, pharmaceutical compositions containing them, and their use in the treatment of airway diseases, inflammatory diseases, copd or asthma |
| WO2009061881A1 (en) * | 2007-11-07 | 2009-05-14 | Glaxo Group Limited | Spirodihydrobenzofurans as modulators of chemokine receptors |
| GB0909768D0 (en) * | 2009-06-08 | 2009-07-22 | Nanyang Polytechnic | Novel compounds and uses thereof |
| WO2023044364A1 (en) | 2021-09-15 | 2023-03-23 | Enko Chem, Inc. | Protoporphyrinogen oxidase inhibitors |
Family Cites Families (28)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US4010201A (en) * | 1974-04-12 | 1977-03-01 | The Upjohn Company | Organic compounds |
| US4166119A (en) | 1978-04-14 | 1979-08-28 | American Hoechst Corporation | Analgesic and tranquilizing spiro[dihydrobenzofuran]piperidines and pyrrolidines |
| US4166120A (en) * | 1978-04-14 | 1979-08-28 | American Hoechst Corporation | Analgesic and tranquilizing benzoylpropyl-spiro[dihydrobenzofuran]piperidines and pyrrolidines |
| US4263317A (en) * | 1979-09-06 | 1981-04-21 | Hoechst-Roussel Pharmaceuticals, Inc. | Spiro[cyclohexane-1,1'(3'H)-isobenzofuran]s |
| US5366986A (en) | 1988-04-15 | 1994-11-22 | T Cell Sciences, Inc. | Compounds which inhibit complement and/or suppress immune activity |
| DE3930262A1 (de) | 1989-09-11 | 1991-03-21 | Thomae Gmbh Dr K | Kondensierte diazepinone, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| US5576321A (en) | 1995-01-17 | 1996-11-19 | Eli Lilly And Company | Compounds having effects on serotonin-related systems |
| ES2191754T3 (es) | 1995-05-18 | 2003-09-16 | Altana Pharma Ag | Fenil-dihidrobenzofuranos. |
| US5962462A (en) * | 1996-12-13 | 1999-10-05 | Merck & Co., Inc. | Spiro-substituted azacycles as modulators of chemokine receptor activity |
| WO1998025605A1 (en) | 1996-12-13 | 1998-06-18 | Merck & Co., Inc. | Spiro-substituted azacycles as modulators of chemokine receptor activity |
| EP1003743A4 (en) | 1997-01-21 | 2001-04-11 | Merck & Co Inc | 3,3-DISBSTITUED PIPERIDINE LIKE MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY |
| DE69922494T2 (de) | 1998-02-04 | 2005-05-25 | Banyu Pharmaceutical Co., Ltd. | Zyklische n-acylamin-derivate |
| US6288083B1 (en) | 1998-09-04 | 2001-09-11 | Millennium Pharmaceuticals, Inc. | Chemokine receptor antagonists and methods of use therefor |
| ATE250604T1 (de) | 1999-10-27 | 2003-10-15 | Millennium Pharm Inc | Pyridyl enthaltende spirocyclische verbindungen als inhibitoren der fibrinogen-abhängigen blutplättchen aggregation |
| AU2001243394A1 (en) * | 2000-03-02 | 2001-09-12 | Smith Kline Beecham Corporation | Compounds and methods |
| AR028948A1 (es) | 2000-06-20 | 2003-05-28 | Astrazeneca Ab | Compuestos novedosos |
| WO2002102387A1 (en) | 2001-06-18 | 2002-12-27 | H. Lundbeck A/S | Treatment of neuropathic pain |
| AU2002363236A1 (en) | 2001-10-30 | 2003-05-12 | Millennium Pharmaceuticals, Inc. | Compounds, pharmaceutical compositions and methods of use therefor |
| SE0202133D0 (sv) * | 2002-07-08 | 2002-07-08 | Astrazeneca Ab | Novel compounds |
| WO2004041279A1 (en) | 2002-10-30 | 2004-05-21 | Merck & Co., Inc. | Gamma-aminoamide modulators of chemokine receptor activity |
| MXPA05005660A (es) * | 2002-11-27 | 2005-10-18 | Incyte Corp | Derivados de 3-aminopirrolidina como moduladores de receptores de quimocina. |
| US20070021498A1 (en) * | 2004-10-14 | 2007-01-25 | Nafizal Hossain | Novel tricyclic spiroderivatives as modulators of chemokine receptor activity |
| SE0302755D0 (sv) * | 2003-10-17 | 2003-10-17 | Astrazeneca Ab | Novel compounds |
| 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 |
| CA2563164A1 (en) | 2004-03-29 | 2005-10-06 | Pfizer Inc. | Alpha aryl or heteroaryl methyl beta piperidino propanoic acid compounds as orl1-receptor antagonists |
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2003
- 2003-11-20 SE SE0303090A patent/SE0303090D0/xx unknown
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2004
- 2004-11-15 NZ NZ547259A patent/NZ547259A/en unknown
- 2004-11-15 JP JP2006541084A patent/JP2007512323A/ja active Pending
- 2004-11-15 CN CNA2004800406429A patent/CN1906200A/zh active Pending
- 2004-11-15 BR BRPI0416745-7A patent/BRPI0416745A/pt not_active IP Right Cessation
- 2004-11-15 KR KR1020067009802A patent/KR20060111518A/ko not_active Withdrawn
- 2004-11-15 CA CA002546028A patent/CA2546028A1/en not_active Abandoned
- 2004-11-15 EP EP04800321A patent/EP1687311A1/en not_active Withdrawn
- 2004-11-15 WO PCT/SE2004/001658 patent/WO2005049620A1/en not_active Ceased
- 2004-11-15 AU AU2004291455A patent/AU2004291455B2/en not_active Ceased
- 2004-11-15 US US10/579,545 patent/US7498338B2/en not_active Expired - Fee Related
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2006
- 2006-05-04 IL IL175437A patent/IL175437A0/en unknown
- 2006-05-18 ZA ZA200604020A patent/ZA200604020B/en unknown
- 2006-06-20 NO NO20062900A patent/NO20062900L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| CN1906200A (zh) | 2007-01-31 |
| BRPI0416745A (pt) | 2007-01-16 |
| EP1687311A1 (en) | 2006-08-09 |
| JP2007512323A (ja) | 2007-05-17 |
| AU2004291455A1 (en) | 2005-06-02 |
| WO2005049620A1 (en) | 2005-06-02 |
| CA2546028A1 (en) | 2005-06-02 |
| NZ547259A (en) | 2009-04-30 |
| SE0303090D0 (sv) | 2003-11-20 |
| IL175437A0 (en) | 2006-09-05 |
| US20070129393A1 (en) | 2007-06-07 |
| NO20062900L (no) | 2006-08-21 |
| AU2004291455B2 (en) | 2008-01-24 |
| KR20060111518A (ko) | 2006-10-27 |
| US7498338B2 (en) | 2009-03-03 |
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