ZA200407414B - Piperidine or 8-aza-bicyclo[3.2.1]oct-3-yl derivatives useful as modulators of chemokine receptor activity (especially CCR5). - Google Patents
Piperidine or 8-aza-bicyclo[3.2.1]oct-3-yl derivatives useful as modulators of chemokine receptor activity (especially CCR5). Download PDFInfo
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- ZA200407414B ZA200407414B ZA200407414A ZA200407414A ZA200407414B ZA 200407414 B ZA200407414 B ZA 200407414B ZA 200407414 A ZA200407414 A ZA 200407414A ZA 200407414 A ZA200407414 A ZA 200407414A ZA 200407414 B ZA200407414 B ZA 200407414B
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- South Africa
- Prior art keywords
- alkyl
- compound
- phenyl
- formula
- heteroaryl
- Prior art date
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- NFIHFQYSYIMSEY-DEOSSOPVSA-N n-[1-[(3s)-3-amino-3-(3-fluorophenyl)propyl]piperidin-4-yl]-n-ethyl-2-(4-methylsulfonylphenyl)acetamide Chemical compound C1([C@@H](N)CCN2CCC(CC2)N(CC)C(=O)CC=2C=CC(=CC=2)S(C)(=O)=O)=CC=CC(F)=C1 NFIHFQYSYIMSEY-DEOSSOPVSA-N 0.000 description 1
- YTQWKGLRUFZULM-UHFFFAOYSA-N n-ethyl-2-(4-methylsulfonylphenyl)acetamide Chemical compound CCNC(=O)CC1=CC=C(S(C)(=O)=O)C=C1 YTQWKGLRUFZULM-UHFFFAOYSA-N 0.000 description 1
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- 125000003884 phenylalkyl group Chemical group 0.000 description 1
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- 239000010452 phosphate Substances 0.000 description 1
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 125000004193 piperazinyl 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
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- 238000003345 scintillation counting Methods 0.000 description 1
- 239000012419 sodium bis(2-methoxyethoxy)aluminum hydride Substances 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000002594 sorbent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- XQYZSLJNDQRADN-UHFFFAOYSA-N tert-butyl 3-(3-fluorophenyl)-3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate Chemical compound CC(C)(C)OC(=O)CC(NC(=O)OC(C)(C)C)C1=CC=CC(F)=C1 XQYZSLJNDQRADN-UHFFFAOYSA-N 0.000 description 1
- LCOYRNJYKWKOHA-LBPRGKRZSA-N tert-butyl n-[(1s)-1-(3-fluorophenyl)-3-hydroxypropyl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@@H](CCO)C1=CC=CC(F)=C1 LCOYRNJYKWKOHA-LBPRGKRZSA-N 0.000 description 1
- FYFPSHBCRNMKES-LBPRGKRZSA-N tert-butyl n-[(1s)-1-(3-fluorophenyl)-3-oxopropyl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@@H](CC=O)C1=CC=CC(F)=C1 FYFPSHBCRNMKES-LBPRGKRZSA-N 0.000 description 1
- HUJZOADYOIHIMU-MHZLTWQESA-N tert-butyl n-[(1s)-3-[4-[ethyl-[2-(4-methylsulfonylphenyl)acetyl]amino]piperidin-1-yl]-1-(3-fluorophenyl)propyl]carbamate Chemical compound C1([C@@H](NC(=O)OC(C)(C)C)CCN2CCC(CC2)N(CC)C(=O)CC=2C=CC(=CC=2)S(C)(=O)=O)=CC=CC(F)=C1 HUJZOADYOIHIMU-MHZLTWQESA-N 0.000 description 1
- MGUDLLMFISQMMP-WOKNPCPGSA-N tert-butyl n-[(1s)-3-[4-[ethyl-[2-(4-methylsulfonylphenyl)acetyl]amino]piperidin-1-yl]-1-phenylbutyl]carbamate Chemical compound C1([C@@H](NC(=O)OC(C)(C)C)CC(C)N2CCC(CC2)N(CC)C(=O)CC=2C=CC(=CC=2)S(C)(=O)=O)=CC=CC=C1 MGUDLLMFISQMMP-WOKNPCPGSA-N 0.000 description 1
- ZGPCDZZHEWGTEU-LBPRGKRZSA-N tert-butyl n-[(1s)-3-oxo-1-phenylpropyl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@@H](CC=O)C1=CC=CC=C1 ZGPCDZZHEWGTEU-LBPRGKRZSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 230000000451 tissue damage Effects 0.000 description 1
- 231100000827 tissue damage Toxicity 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
- MBYLVOKEDDQJDY-UHFFFAOYSA-N tris(2-aminoethyl)amine Chemical compound NCCN(CCN)CCN MBYLVOKEDDQJDY-UHFFFAOYSA-N 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
- C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
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- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
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- A—HUMAN NECESSITIES
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- 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
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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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
- A61P37/02—Immunomodulators
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Virology (AREA)
- Pulmonology (AREA)
- Rheumatology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Transplantation (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Molecular Biology (AREA)
- AIDS & HIV (AREA)
- Pain & Pain Management (AREA)
- Tropical Medicine & Parasitology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0200919A SE0200919D0 (sv) | 2002-03-25 | 2002-03-25 | Chemical compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200407414B true ZA200407414B (en) | 2005-08-29 |
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Country Status (16)
| Country | Link |
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| US (1) | US20050171353A1 (es) |
| EP (1) | EP1490336A1 (es) |
| JP (1) | JP2005526797A (es) |
| KR (1) | KR20040094876A (es) |
| CN (1) | CN1642913A (es) |
| AR (1) | AR039125A1 (es) |
| AU (1) | AU2003216012A1 (es) |
| BR (1) | BR0308592A (es) |
| CA (1) | CA2479887A1 (es) |
| IL (1) | IL163896A0 (es) |
| MX (1) | MXPA04009162A (es) |
| NO (1) | NO20044545L (es) |
| SE (1) | SE0200919D0 (es) |
| TW (1) | TW200305417A (es) |
| WO (1) | WO2003080574A1 (es) |
| ZA (1) | ZA200407414B (es) |
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| AR028948A1 (es) | 2000-06-20 | 2003-05-28 | Astrazeneca Ab | Compuestos novedosos |
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| SE0302090D0 (sv) * | 2003-07-16 | 2003-07-16 | Astrazeneca Ab | Chemical compounds |
| US7498346B2 (en) * | 2003-12-11 | 2009-03-03 | Genzyme Corporation | Chemokine receptor binding compounds |
| SE0303396D0 (sv) * | 2003-12-16 | 2003-12-16 | Astrazeneca Ab | Chemical compounds |
| TW200538098A (en) * | 2004-03-22 | 2005-12-01 | Astrazeneca Ab | Therapeutic agents |
| ES2277745B1 (es) * | 2005-06-14 | 2008-06-01 | Laboratorios Almirall S.A. | Derivados n-amida de 8-azabiciclo /3.2.1/oct-3-ilo como antagonistas de ccr1. |
| JP2008543858A (ja) * | 2005-06-15 | 2008-12-04 | ジェンザイム・コーポレーション | ケモカインレセプター結合化合物 |
| MX2008001067A (es) * | 2005-08-01 | 2008-03-19 | Astrazeneca Ab | Derivados de piperidina novedosos como moduladores de receptor de quimioquina utiles para el tratamiento de enfermedades respiratorias. |
| BRPI0617720A2 (pt) | 2005-10-19 | 2011-08-02 | Hoffmann La Roche | compostos inibidores de nnrt de fenil-acetamida, usos dos referidos compostos e composição farmacêutica que os contém |
| CA2658984C (en) | 2006-08-16 | 2014-12-02 | Joshua Kennedy-Smith | Non-nucleoside reverse transcriptase inhibitors |
| BRPI0720436A2 (pt) | 2006-12-13 | 2014-01-07 | Hoffmann La Roche | Inibidores de transcriptase reversa de não-nucleosídeo |
| WO2009010478A2 (en) * | 2007-07-13 | 2009-01-22 | Euroscreen S.A. | Use of piperidine derivatives as agonists of chemokine receptor activity |
| CN101412692B (zh) * | 2007-10-18 | 2012-10-17 | 中国科学院上海药物研究所 | 1-(3-氨基丙基)哌啶-4-氨基酰胺类化合物、其药物组合物及其制备方法和用途 |
| CN101712679B (zh) | 2008-10-08 | 2013-04-10 | 中国科学院上海药物研究所 | 一种酰胺类化合物、其药物组合物及其制备方法和用途 |
| CN102140104B (zh) * | 2010-02-03 | 2014-11-12 | 中国科学院上海药物研究所 | 1-(3-(s)-氨基丙基)-哌啶-4-氨基酰胺类化合物、其药物组合物及其制备方法和用途 |
| WO2012113103A1 (en) | 2011-02-25 | 2012-08-30 | Helsinn Healthcare S.A. | Asymmetric ureas and medical uses thereof |
| CN106977511B (zh) * | 2011-12-19 | 2019-04-12 | 中国科学院上海药物研究所 | 一种氨基丙基取代托烷胺类化合物、其药物组合物及其制备方法和用途 |
| CA3017048C (en) | 2016-03-22 | 2023-11-07 | Helsinn Healthcare Sa | Benzenesulfonyl-asymmetric ureas and medical uses thereof |
| US11629196B2 (en) | 2020-04-27 | 2023-04-18 | Incelldx, Inc. | Method of treating SARS-CoV-2-associated hypercytokinemia by administering a human monoclonal antibody (PRO-140) that inhibits CCR5/CCL5 binding interactions |
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| EP1013276A1 (en) * | 1998-12-23 | 2000-06-28 | Pfizer Inc. | Aminoazacycloalkanes as CCR5 modulators |
| AU5473800A (en) * | 1999-06-11 | 2001-01-02 | Merck & Co., Inc. | Cyclopentyl modulators of chemokine receptor activity |
| SE9902987D0 (sv) * | 1999-08-24 | 1999-08-24 | Astra Pharma Prod | Novel compounds |
| GB0011838D0 (en) * | 2000-05-17 | 2000-07-05 | Astrazeneca Ab | Chemical compounds |
| SI1284974T1 (en) * | 2000-05-26 | 2004-08-31 | Pfizer Inc. | Triazolyl tropane derivatives as ccr5 modulators |
| US20040110952A1 (en) * | 2001-03-01 | 2004-06-10 | Jeremy Burrows | N-4-piperidinyl compounds as ccr5 modulators |
| GB0107228D0 (en) * | 2001-03-22 | 2001-05-16 | Astrazeneca Ab | Chemical compounds |
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- 2003-03-24 BR BR0308592-9A patent/BR0308592A/pt not_active Application Discontinuation
- 2003-03-24 JP JP2003578329A patent/JP2005526797A/ja active Pending
- 2003-03-24 AU AU2003216012A patent/AU2003216012A1/en not_active Abandoned
- 2003-03-25 AR ARP030101026A patent/AR039125A1/es unknown
-
2004
- 2004-09-15 ZA ZA200407414A patent/ZA200407414B/en unknown
- 2004-10-22 NO NO20044545A patent/NO20044545L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| MXPA04009162A (es) | 2004-12-07 |
| AR039125A1 (es) | 2005-02-09 |
| AU2003216012A1 (en) | 2003-10-08 |
| IL163896A0 (en) | 2005-12-18 |
| KR20040094876A (ko) | 2004-11-10 |
| TW200305417A (en) | 2003-11-01 |
| NO20044545L (no) | 2004-12-13 |
| CA2479887A1 (en) | 2003-10-02 |
| EP1490336A1 (en) | 2004-12-29 |
| WO2003080574A1 (en) | 2003-10-02 |
| SE0200919D0 (sv) | 2002-03-25 |
| JP2005526797A (ja) | 2005-09-08 |
| CN1642913A (zh) | 2005-07-20 |
| US20050171353A1 (en) | 2005-08-04 |
| BR0308592A (pt) | 2005-02-09 |
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