ZA200103942B - Pyrrolidine derivatives-CCR-3 receptor antagonists. - Google Patents
Pyrrolidine derivatives-CCR-3 receptor antagonists. Download PDFInfo
- Publication number
- ZA200103942B ZA200103942B ZA200103942A ZA200103942A ZA200103942B ZA 200103942 B ZA200103942 B ZA 200103942B ZA 200103942 A ZA200103942 A ZA 200103942A ZA 200103942 A ZA200103942 A ZA 200103942A ZA 200103942 B ZA200103942 B ZA 200103942B
- Authority
- ZA
- South Africa
- Prior art keywords
- compound
- formula
- alkyl
- optionally substituted
- hydrogen
- Prior art date
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- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical class C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 title description 4
- 239000002464 receptor antagonist Substances 0.000 title description 4
- 229940044551 receptor antagonist Drugs 0.000 title description 4
- -1 hydroxy, amino Chemical group 0.000 claims description 100
- 150000001875 compounds Chemical class 0.000 claims description 92
- 125000000217 alkyl group Chemical group 0.000 claims description 71
- 229910052739 hydrogen Inorganic materials 0.000 claims description 53
- 239000001257 hydrogen Substances 0.000 claims description 53
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 38
- 125000001188 haloalkyl group Chemical group 0.000 claims description 35
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 33
- 125000004432 carbon atom Chemical group C* 0.000 claims description 25
- 125000001072 heteroaryl group Chemical group 0.000 claims description 24
- 125000001424 substituent group Chemical group 0.000 claims description 21
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 19
- 201000010099 disease Diseases 0.000 claims description 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 125000002947 alkylene group Chemical group 0.000 claims description 10
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 8
- 125000002252 acyl group Chemical group 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 7
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
- 241000124008 Mammalia Species 0.000 claims description 6
- 208000006673 asthma Diseases 0.000 claims description 6
- 125000001246 bromo group Chemical group Br* 0.000 claims description 6
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 229940002612 prodrug Drugs 0.000 claims description 6
- 239000000651 prodrug Substances 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 125000004419 alkynylene group Chemical group 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 4
- 125000004450 alkenylene group Chemical group 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 2
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 2
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims 3
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- 239000002168 alkylating agent Substances 0.000 claims 3
- 229940100198 alkylating agent Drugs 0.000 claims 3
- 230000002152 alkylating effect Effects 0.000 claims 3
- 239000007822 coupling agent Substances 0.000 claims 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 3
- NDZYPHLNJZSQJY-QNWVGRARSA-N 1-(5-acetyl-4-methyl-1,3-thiazol-2-yl)-3-[(1r,2s)-2-[[(3s)-3-[(4-fluorophenyl)methyl]piperidin-1-yl]methyl]cyclohexyl]urea Chemical compound CC1=C(C(=O)C)SC(NC(=O)N[C@H]2[C@@H](CCCC2)CN2C[C@H](CC=3C=CC(F)=CC=3)CCC2)=N1 NDZYPHLNJZSQJY-QNWVGRARSA-N 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
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- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 2
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- 239000004480 active ingredient Substances 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
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- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical group OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
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- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 1
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Classifications
-
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
- C07D207/09—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pulmonology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10929798P | 1998-11-20 | 1998-11-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200103942B true ZA200103942B (en) | 2002-08-15 |
Family
ID=22326918
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200103942A ZA200103942B (en) | 1998-11-20 | 2001-05-15 | Pyrrolidine derivatives-CCR-3 receptor antagonists. |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US6166015A (pt) |
| EP (1) | EP1131288A1 (pt) |
| JP (1) | JP3593037B2 (pt) |
| KR (1) | KR20010086045A (pt) |
| CN (1) | CN1158256C (pt) |
| AR (1) | AR023707A1 (pt) |
| AU (1) | AU763960B2 (pt) |
| BR (1) | BR9915520A (pt) |
| CA (1) | CA2350903A1 (pt) |
| CO (1) | CO5140119A1 (pt) |
| CZ (1) | CZ20011760A3 (pt) |
| DE (1) | DE19955794A1 (pt) |
| ES (1) | ES2158814B1 (pt) |
| FR (1) | FR2786185A1 (pt) |
| GB (1) | GB2343893B (pt) |
| HU (1) | HUP0104364A2 (pt) |
| ID (1) | ID29067A (pt) |
| IL (1) | IL143226A0 (pt) |
| IT (1) | IT1307900B1 (pt) |
| MA (1) | MA26762A1 (pt) |
| NO (1) | NO20012411L (pt) |
| PE (1) | PE20001403A1 (pt) |
| PL (1) | PL348375A1 (pt) |
| TR (1) | TR200101398T2 (pt) |
| UY (1) | UY25811A1 (pt) |
| WO (1) | WO2000031032A1 (pt) |
| ZA (1) | ZA200103942B (pt) |
Families Citing this family (49)
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| IL125658A0 (en) | 1997-08-18 | 1999-04-11 | Hoffmann La Roche | Ccr-3 receptor antagonists |
| US6339087B1 (en) | 1997-08-18 | 2002-01-15 | Syntex (U.S.A.) Llc | Cyclic amine derivatives-CCR-3 receptor antagonists |
| US6316623B1 (en) * | 1998-08-21 | 2001-11-13 | Isis Pharmaceuticals, Inc. | Ethylenediamine compound libraries |
| TR200101397T2 (tr) | 1998-11-20 | 2001-11-21 | F.Hoffmann-La Roche Ag | Piperidin CCR-3 reseptörü antagonistleri |
| NZ515374A (en) | 1999-05-18 | 2004-09-24 | Teijin Ltd | Remedies or prophylactics for diseases in association with chemokines |
| AU779610B2 (en) * | 1999-08-04 | 2005-02-03 | Teijin Limited | Cyclic amine CCR3 antagonists |
| EP1238970B9 (en) * | 1999-12-08 | 2007-05-09 | Teijin Limited | Cycloamine ccr5 receptor antagonists |
| PL362984A1 (en) * | 2000-09-29 | 2004-11-15 | Glaxo Group Limited | Compounds useful in the treatment of inflammatory diseases |
| KR20030031198A (ko) | 2000-09-29 | 2003-04-18 | 글락소 그룹 리미티드 | 염증 질환 치료용 모르폴린-아세트아미드 유도체 |
| KR20030061455A (ko) | 2000-12-19 | 2003-07-18 | 에프. 호프만-라 로슈 아게 | Ｃｃｒ-3 수용체 길항제로서의 치환된 피롤리딘 |
| FR2821356A1 (fr) | 2001-02-23 | 2002-08-30 | Cerep | Nouveaux derives d'arylcarbamates et d'arylurees, preparations et utilisations |
| GB0117387D0 (en) * | 2001-07-17 | 2001-09-05 | Novartis Ag | Organic compounds |
| MXPA04001977A (es) * | 2001-09-13 | 2004-06-07 | Hoffmann La Roche | Antagonistas v de receptor ccr-3. |
| US7067549B2 (en) * | 2001-12-31 | 2006-06-27 | Actelion Pharmaceuticals Ag | Pyrrolidone carboxamides |
| GB0207436D0 (en) * | 2002-03-28 | 2002-05-08 | Glaxo Group Ltd | Novel compounds |
| GB0207432D0 (en) | 2002-03-28 | 2002-05-08 | Glaxo Group Ltd | Novel compounds |
| GB0207443D0 (en) * | 2002-03-28 | 2002-05-08 | Glaxo Group Ltd | Novel compounds |
| GB0207439D0 (en) * | 2002-03-28 | 2002-05-08 | Glaxo Group Ltd | Novel compounds |
| GB0212355D0 (en) * | 2002-05-29 | 2002-07-10 | Glaxo Group Ltd | Novel compounds |
| US7589199B2 (en) | 2002-06-12 | 2009-09-15 | Chemocentryx, Inc. | Substituted piperazines |
| US7842693B2 (en) | 2002-06-12 | 2010-11-30 | Chemocentryx, Inc. | Substituted piperazines |
| ATE438401T1 (de) | 2002-06-12 | 2009-08-15 | Chemocentryx Inc | 1-aryl-4-substituierte piperazin-derivate zur verwendung als ccr1-antagonisten zur behandlung von entzündungen und immunerkrankungen |
| JP2006502107A (ja) | 2002-07-02 | 2006-01-19 | エフ．ホフマン−ラ ロシュ アーゲー | Ｃｃｒ−３レセプターアンタゴニストｉｘとしての２，５−置換ピリミジン誘導体 |
| US6919356B2 (en) * | 2002-09-26 | 2005-07-19 | Bristol Myers Squibb Company | N-substituted heterocyclic amines as modulators of chemokine receptor activity |
| DE602004022783D1 (de) | 2003-03-06 | 2009-10-08 | Glaxo Group Ltd | Heterozyklische harnstoff-derivate für die behandlung von schmerzen. |
| WO2004078744A2 (en) | 2003-03-07 | 2004-09-16 | Glaxo Group Limited | Urea derivatives and their use as vanilloid receptor antagonists in the treatment of pain |
| GB0305426D0 (en) * | 2003-03-08 | 2003-04-16 | Glaxo Group Ltd | Novel compounds |
| WO2004080966A1 (ja) | 2003-03-14 | 2004-09-23 | Ono Pharmaceutical Co., Ltd. | 含窒素複素環誘導体およびそれらを有効成分とする薬剤 |
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-
1999
- 1999-11-11 AU AU13825/00A patent/AU763960B2/en not_active Ceased
- 1999-11-11 PL PL99348375A patent/PL348375A1/xx not_active Application Discontinuation
- 1999-11-11 KR KR1020017006362A patent/KR20010086045A/ko not_active Application Discontinuation
- 1999-11-11 CA CA002350903A patent/CA2350903A1/en not_active Abandoned
- 1999-11-11 JP JP2000583860A patent/JP3593037B2/ja not_active Expired - Fee Related
- 1999-11-11 ID IDW00200101080A patent/ID29067A/id unknown
- 1999-11-11 CN CNB99813287XA patent/CN1158256C/zh not_active Expired - Fee Related
- 1999-11-11 CZ CZ20011760A patent/CZ20011760A3/cs unknown
- 1999-11-11 TR TR2001/01398T patent/TR200101398T2/xx unknown
- 1999-11-11 WO PCT/EP1999/008665 patent/WO2000031032A1/en not_active Application Discontinuation
- 1999-11-11 IL IL14322699A patent/IL143226A0/xx unknown
- 1999-11-11 EP EP99972623A patent/EP1131288A1/en not_active Withdrawn
- 1999-11-11 BR BR9915520-6A patent/BR9915520A/pt not_active IP Right Cessation
- 1999-11-11 HU HU0104364A patent/HUP0104364A2/hu unknown
- 1999-11-16 PE PE1999001161A patent/PE20001403A1/es not_active Application Discontinuation
- 1999-11-17 GB GB9927227A patent/GB2343893B/en not_active Expired - Fee Related
- 1999-11-18 AR ARP990105860A patent/AR023707A1/es unknown
- 1999-11-18 FR FR9914495A patent/FR2786185A1/fr not_active Withdrawn
- 1999-11-18 US US09/442,656 patent/US6166015A/en not_active Expired - Fee Related
- 1999-11-18 CO CO99072639A patent/CO5140119A1/es unknown
- 1999-11-19 IT IT1999TO001009A patent/IT1307900B1/it active
- 1999-11-19 DE DE19955794A patent/DE19955794A1/de not_active Withdrawn
- 1999-11-19 UY UY25811A patent/UY25811A1/es unknown
- 1999-11-19 ES ES009902547A patent/ES2158814B1/es not_active Withdrawn - After Issue
-
2001
- 2001-05-15 ZA ZA200103942A patent/ZA200103942B/en unknown
- 2001-05-16 NO NO20012411A patent/NO20012411L/no not_active Application Discontinuation
- 2001-05-17 MA MA26199A patent/MA26762A1/fr unknown
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