ZA200304530B - Substituted pyrrolidines as CCR-3 receptor antagonists. - Google Patents
Substituted pyrrolidines as CCR-3 receptor antagonists. Download PDFInfo
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- ZA200304530B ZA200304530B ZA200304530A ZA200304530A ZA200304530B ZA 200304530 B ZA200304530 B ZA 200304530B ZA 200304530 A ZA200304530 A ZA 200304530A ZA 200304530 A ZA200304530 A ZA 200304530A ZA 200304530 B ZA200304530 B ZA 200304530B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkyl
- compound
- formula
- hydrogen
- alk
- Prior art date
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- 102000004499 CCR3 Receptors Human genes 0.000 title claims description 14
- 108010017316 CCR3 Receptors Proteins 0.000 title claims description 14
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- 229940044551 receptor antagonist Drugs 0.000 title claims description 8
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- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- HOGSZOOQFYPUAV-IUFJOMBNSA-N n-[2-[(2s,4r)-4-[(3,4-dichlorophenyl)methyl]pyrrolidin-2-yl]ethyl]-2-(5-phenylpyrimidin-2-yl)sulfanylacetamide;hydrochloride Chemical compound Cl.C1=C(Cl)C(Cl)=CC=C1C[C@@H]1C[C@@H](CCNC(=O)CSC=2N=CC(=CN=2)C=2C=CC=CC=2)NC1 HOGSZOOQFYPUAV-IUFJOMBNSA-N 0.000 description 1
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- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
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- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 230000008506 pathogenesis Effects 0.000 description 1
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- 239000000312 peanut oil Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
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- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
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- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- WSHYKIAQCMIPTB-UHFFFAOYSA-M potassium;2-oxo-3-(3-oxo-1-phenylbutyl)chromen-4-olate Chemical compound [K+].[O-]C=1C2=CC=CC=C2OC(=O)C=1C(CC(=O)C)C1=CC=CC=C1 WSHYKIAQCMIPTB-UHFFFAOYSA-M 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
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- 201000009732 pulmonary eosinophilia Diseases 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
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- AUKXFNABVHIUAC-UHFFFAOYSA-N pyrrolidin-2-ylmethylamine Chemical class NCC1CCCN1 AUKXFNABVHIUAC-UHFFFAOYSA-N 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
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- 206010039083 rhinitis Diseases 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000012163 sequencing technique Methods 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 235000020183 skimmed milk Nutrition 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007974 sodium acetate buffer Substances 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- BAZAXWOYCMUHIX-UHFFFAOYSA-M sodium perchlorate Chemical compound [Na+].[O-]Cl(=O)(=O)=O BAZAXWOYCMUHIX-UHFFFAOYSA-M 0.000 description 1
- 229910001488 sodium perchlorate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- IXGNPUSUVRTQGW-UHFFFAOYSA-M sodium;perchlorate;hydrate Chemical compound O.[Na+].[O-]Cl(=O)(=O)=O IXGNPUSUVRTQGW-UHFFFAOYSA-M 0.000 description 1
- 238000000527 sonication Methods 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
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- 239000008117 stearic acid Substances 0.000 description 1
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- 230000000153 supplemental effect Effects 0.000 description 1
- MDKGKXOCJGEUJW-UHFFFAOYSA-N suprofen Chemical compound C1=CC(C(C(O)=O)C)=CC=C1C(=O)C1=CC=CS1 MDKGKXOCJGEUJW-UHFFFAOYSA-N 0.000 description 1
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- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- CAHOUDZKOBNBED-KGLIPLIRSA-N tert-butyl (2s,4r)-4-[(3,4-dichlorophenyl)methyl]-2-(methylsulfonyloxymethyl)pyrrolidine-1-carboxylate Chemical compound C1[C@@H](COS(C)(=O)=O)N(C(=O)OC(C)(C)C)C[C@@H]1CC1=CC=C(Cl)C(Cl)=C1 CAHOUDZKOBNBED-KGLIPLIRSA-N 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
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- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 150000008648 triflates Chemical class 0.000 description 1
- PNQBEPDZQUOCNY-UHFFFAOYSA-N trifluoroacetyl chloride Chemical compound FC(F)(F)C(Cl)=O PNQBEPDZQUOCNY-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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US25658500P | 2000-12-19 | 2000-12-19 |
Publications (1)
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ZA200304530B true ZA200304530B (en) | 2004-09-10 |
Family
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Application Number | Title | Priority Date | Filing Date |
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ZA200304530A ZA200304530B (en) | 2000-12-19 | 2003-06-10 | Substituted pyrrolidines as CCR-3 receptor antagonists. |
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US (2) | US6552028B2 (de) |
EP (1) | EP1358181B1 (de) |
JP (1) | JP2004519443A (de) |
KR (1) | KR20030061455A (de) |
CN (1) | CN1239498C (de) |
AR (1) | AR035519A1 (de) |
AT (1) | ATE374198T1 (de) |
AU (1) | AU2002216107A1 (de) |
BR (1) | BR0116352A (de) |
CA (1) | CA2431767A1 (de) |
DE (1) | DE60130684T2 (de) |
ES (1) | ES2292530T3 (de) |
MX (1) | MXPA03005581A (de) |
WO (1) | WO2002050064A1 (de) |
ZA (1) | ZA200304530B (de) |
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Publication number | Priority date | Publication date | Assignee | Title |
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MXPA06004304A (es) * | 2003-10-24 | 2006-06-05 | Hoffmann La Roche | Antagonistas del receptor ccr-3. |
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CA2143143A1 (en) * | 1994-03-08 | 1995-09-09 | Toshihiko Tanaka | 3-phenylpyrrolidine derivatives |
IL125658A0 (en) * | 1997-08-18 | 1999-04-11 | Hoffmann La Roche | Ccr-3 receptor antagonists |
AU763960B2 (en) * | 1998-11-20 | 2003-08-07 | F. Hoffmann-La Roche Ag | Pyrrolidine derivatives-CCR-3 receptor antagonists |
BR9915735A (pt) * | 1998-11-20 | 2001-09-04 | Hoffmann La Roche | Antagonistas receptores de ccr-3 de piperidina |
WO2000035449A1 (en) | 1998-12-18 | 2000-06-22 | Du Pont Pharmaceuticals Company | N-ureidoalkyl-piperidines as modulators of chemokine receptor activity |
IL142768A0 (en) | 1998-12-18 | 2002-03-10 | Du Pont Pharm Co | N-ureidoalkyl-piperidines as modulators of chemokine receptor activity |
AU2056700A (en) | 1998-12-18 | 2000-07-03 | Du Pont Pharmaceuticals Company | 2-substituted-4-nitrogen heterocycles as modulators of chemokine receptor activity |
CA2350730A1 (en) | 1998-12-18 | 2000-06-22 | George V. Delucca | N-ureidoalkyl-piperidines as modulators of chemokine receptor activity |
EP1140087A4 (de) | 1998-12-18 | 2002-04-03 | Du Pont Pharm Co | N-ureidoalkyl-piperidine als modulatoren der chemokin-rezeptor-aktivität |
US6331545B1 (en) | 1998-12-18 | 2001-12-18 | Soo S. Ko | Heterocycyclic piperidines as modulators of chemokine receptor activity |
CA2347909A1 (en) | 1998-12-18 | 2000-06-22 | Joseph B. Santella, Iii | N-ureidoalkyl-piperidines as modulators of chemokine receptor activity |
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2001
- 2001-12-13 CN CNB018208789A patent/CN1239498C/zh not_active Expired - Fee Related
- 2001-12-13 DE DE60130684T patent/DE60130684T2/de not_active Expired - Fee Related
- 2001-12-13 MX MXPA03005581A patent/MXPA03005581A/es active IP Right Grant
- 2001-12-13 EP EP01271370A patent/EP1358181B1/de not_active Expired - Lifetime
- 2001-12-13 JP JP2002551560A patent/JP2004519443A/ja active Pending
- 2001-12-13 CA CA002431767A patent/CA2431767A1/en not_active Abandoned
- 2001-12-13 ES ES01271370T patent/ES2292530T3/es not_active Expired - Lifetime
- 2001-12-13 AU AU2002216107A patent/AU2002216107A1/en not_active Abandoned
- 2001-12-13 KR KR10-2003-7008134A patent/KR20030061455A/ko not_active Application Discontinuation
- 2001-12-13 WO PCT/EP2001/014670 patent/WO2002050064A1/en active IP Right Grant
- 2001-12-13 AT AT01271370T patent/ATE374198T1/de not_active IP Right Cessation
- 2001-12-13 BR BR0116352-3A patent/BR0116352A/pt not_active IP Right Cessation
- 2001-12-17 AR ARP010105833A patent/AR035519A1/es not_active Application Discontinuation
- 2001-12-19 US US10/034,034 patent/US6552028B2/en not_active Expired - Fee Related
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2003
- 2003-02-18 US US10/368,097 patent/US20030199532A1/en not_active Abandoned
- 2003-06-10 ZA ZA200304530A patent/ZA200304530B/en unknown
Also Published As
Publication number | Publication date |
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WO2002050064A1 (en) | 2002-06-27 |
AU2002216107A1 (en) | 2002-07-01 |
MXPA03005581A (es) | 2003-10-06 |
CN1481379A (zh) | 2004-03-10 |
CN1239498C (zh) | 2006-02-01 |
DE60130684T2 (de) | 2008-08-14 |
AR035519A1 (es) | 2004-06-02 |
EP1358181A1 (de) | 2003-11-05 |
KR20030061455A (ko) | 2003-07-18 |
ATE374198T1 (de) | 2007-10-15 |
BR0116352A (pt) | 2003-12-02 |
JP2004519443A (ja) | 2004-07-02 |
ES2292530T3 (es) | 2008-03-16 |
US20030199532A1 (en) | 2003-10-23 |
CA2431767A1 (en) | 2002-06-27 |
US6552028B2 (en) | 2003-04-22 |
DE60130684D1 (de) | 2007-11-08 |
EP1358181B1 (de) | 2007-09-26 |
US20020198255A1 (en) | 2002-12-26 |
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