ZA200604020B - Novel compounds - Google Patents

Novel compounds Download PDF

Info

Publication number: ZA200604020B
Authority: ZA; South Africa
Prior art keywords: chloro; benzofuran; piperidin; spiro; propan
Prior art date: 2003-11-20

Application number

ZA200604020A

Other languages

English (en)

Inventor

Baxter Andrew

Ivanova Svetlana

Pimm Austen

Hossain Nafizal

Mensonides-Harsema Marguerite

Reuberson James

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.)

2003-11-20

Filing date

2006-05-18

Publication date

2007-12-27

2006-05-18 Application filed by Astrazeneca Ab filed Critical Astrazeneca Ab

2007-12-27 Publication of ZA200604020B publication Critical patent/ZA200604020B/en

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
102000019034 Chemokines Human genes 0.000 description 3
108010012236 Chemokines Proteins 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
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
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125000000719 pyrrolidinyl group Chemical group 0.000 description 3
102000005962 receptors Human genes 0.000 description 3
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
102000004890 Interleukin-8 Human genes 0.000 description 2
108090001007 Interleukin-8 Proteins 0.000 description 2
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
125000004432 carbon atom Chemical group C* 0.000 description 2
239000002975 chemoattractant Substances 0.000 description 2
108010035886 connective tissue-activating peptide Proteins 0.000 description 2
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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125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 description 2
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125000005843 halogen group Chemical group 0.000 description 2
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
229940096397 interleukin-8 Drugs 0.000 description 2
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
210000000440 neutrophil Anatomy 0.000 description 2
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125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
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102000019388 CXC chemokine Human genes 0.000 description 1
102100023688 Eotaxin Human genes 0.000 description 1
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125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
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125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 description 1
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238000003780 insertion Methods 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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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
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- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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- 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]
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- 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)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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ZA200604020A 2003-11-20 2006-05-18 Novel compounds ZA200604020B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
SE0303090A SE0303090D0 (sv)	2003-11-20	2003-11-20	Novel compounds

Publications (1)

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ZA200604020B true ZA200604020B (en)	2007-12-27

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ID=29729113

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ZA200604020A ZA200604020B (en)	2003-11-20	2006-05-18	Novel compounds

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US (1)	US7498338B2 (ja)
EP (1)	EP1687311A1 (ja)
JP (1)	JP2007512323A (ja)
KR (1)	KR20060111518A (ja)
CN (1)	CN1906200A (ja)
AU (1)	AU2004291455B2 (ja)
BR (1)	BRPI0416745A (ja)
CA (1)	CA2546028A1 (ja)
IL (1)	IL175437A0 (ja)
NO (1)	NO20062900L (ja)
NZ (1)	NZ547259A (ja)
SE (1)	SE0303090D0 (ja)
WO (1)	WO2005049620A1 (ja)
ZA (1)	ZA200604020B (ja)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
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
AU2007212293A1 (en) *	2006-02-08	2007-08-16	Wyeth	Sulfonamide derivatives to treat infection with hepatitis C virus
AU2007275931B2 (en) *	2006-07-19	2011-06-16	Astrazeneca Ab	Novel tricyclic spiropiperidine compounds, their synthesis and their uses as modulators of chemokine receptor activity
WO2008103125A1 (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
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
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
WO2009011654A1 (en) *	2007-07-17	2009-01-22	Astrazeneca Ab	Process for the preparation of cyclic spiropiperidines
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)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
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
CA2221357A1 (en)	1995-05-18	1996-11-21	Byk Gulden Lomberg Chemische Fabrik Gmbh	Phenyl dihydrobenzofuranes
US5962462A (en) *	1996-12-13	1999-10-05	Merck & Co., Inc.	Spiro-substituted azacycles as modulators of chemokine receptor activity
AU5803398A (en) *	1996-12-13	1998-07-03	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
EP1061076B1 (en)	1998-02-04	2004-12-08	Banyu Pharmaceutical Co., Ltd.	N-acyl cyclic amine derivatives
US6288083B1 (en)	1998-09-04	2001-09-11	Millennium Pharmaceuticals, Inc.	Chemokine receptor antagonists and methods of use therefor
JP2003514777A (ja)	1999-10-27	2003-04-22	シーオーアールセラピューティクスインコーポレイテッド	フィブリノゲン依存性血小板凝集の阻害剤としてのピリジル含有スピロ環化合物
WO2001064213A1 (en)	2000-03-02	2001-09-07	Smithkline 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
JP2006511500A (ja)	2002-10-30	2006-04-06	メルク　エンド　カムパニー　インコーポレーテッド	γ−アミノアミド系のケモカイン受容体活性調節剤
EP2431357A3 (en) *	2002-11-27	2012-08-22	Incyte Corporation	3-Aminopyrrolidine Derivatives as Modulators of Chemokine Receptors
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

2003
- 2003-11-20 SE SE0303090A patent/SE0303090D0/xx unknown
2004
- 2004-11-15 CA CA002546028A patent/CA2546028A1/en not_active Abandoned
- 2004-11-15 AU AU2004291455A patent/AU2004291455B2/en not_active Ceased
- 2004-11-15 JP JP2006541084A patent/JP2007512323A/ja active Pending
- 2004-11-15 KR KR1020067009802A patent/KR20060111518A/ko not_active Application Discontinuation
- 2004-11-15 WO PCT/SE2004/001658 patent/WO2005049620A1/en active Application Filing
- 2004-11-15 NZ NZ547259A patent/NZ547259A/en unknown
- 2004-11-15 CN CNA2004800406429A patent/CN1906200A/zh active Pending
- 2004-11-15 US US10/579,545 patent/US7498338B2/en not_active Expired - Fee Related
- 2004-11-15 EP EP04800321A patent/EP1687311A1/en not_active Withdrawn
- 2004-11-15 BR BRPI0416745-7A patent/BRPI0416745A/pt not_active IP Right Cessation
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
WO2005049620A1 (en)	2005-06-02
US20070129393A1 (en)	2007-06-07
CN1906200A (zh)	2007-01-31
US7498338B2 (en)	2009-03-03
AU2004291455B2 (en)	2008-01-24
IL175437A0 (en)	2006-09-05
EP1687311A1 (en)	2006-08-09
NO20062900L (no)	2006-08-21
SE0303090D0 (sv)	2003-11-20
CA2546028A1 (en)	2005-06-02
BRPI0416745A (pt)	2007-01-16
KR20060111518A (ko)	2006-10-27
JP2007512323A (ja)	2007-05-17
AU2004291455A1 (en)	2005-06-02
NZ547259A (en)	2009-04-30

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