HRP20040940A2 - Tropane derivatives as ccr5 modulators - Google Patents

Tropane derivatives as ccr5 modulators Download PDF

Info

Publication number: HRP20040940A2
Authority: HR; Croatia
Prior art keywords: alkyl; compound; formula; image; mmol
Prior art date: 2002-04-08

Application number

HR20040940A

Other languages

English (en)

Croatian (hr)

Inventor

Ann Basford Patricia

Thomas Stephenson Peter

Colin John Taylor Stefan

Wood Anthony

Original Assignee

Pfizer Inc.

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.)

2002-04-08

Filing date

2004-10-07

Publication date

2005-04-30

2002-04-08 Priority claimed from GBGB0208071.1A external-priority patent/GB0208071D0/en

2003-01-23 Priority claimed from GB0301575A external-priority patent/GB0301575D0/en

2004-10-07 Application filed by Pfizer Inc. filed Critical Pfizer Inc.

2005-04-30 Publication of HRP20040940A2 publication Critical patent/HRP20040940A2/hr

Links

150000003813 tropane derivatives Chemical class 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 299
125000000217 alkyl group Chemical group 0.000 claims description 63
238000000034 method Methods 0.000 claims description 57
150000003839 salts Chemical class 0.000 claims description 49
229920006395 saturated elastomer Polymers 0.000 claims description 45
239000012453 solvate Substances 0.000 claims description 37
125000001153 fluoro group Chemical group F* 0.000 claims description 28
238000011282 treatment Methods 0.000 claims description 24
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
239000003814 drug Substances 0.000 claims description 17
125000000623 heterocyclic group Chemical group 0.000 claims description 16
125000004429 atom Chemical group 0.000 claims description 13
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
101100134922 Gallus gallus COR5 gene Proteins 0.000 claims description 11
229910052736 halogen Inorganic materials 0.000 claims description 11
150000002367 halogens Chemical class 0.000 claims description 11
208000015181 infectious disease Diseases 0.000 claims description 11
208000031886 HIV Infections Diseases 0.000 claims description 10
229910052739 hydrogen Inorganic materials 0.000 claims description 10
229910052760 oxygen Inorganic materials 0.000 claims description 10
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 9
208000027866 inflammatory disease Diseases 0.000 claims description 9
125000006239 protecting group Chemical group 0.000 claims description 9
229910052717 sulfur Inorganic materials 0.000 claims description 9
101100440695 Dictyostelium discoideum corB gene Proteins 0.000 claims description 8
208000037357 HIV infectious disease Diseases 0.000 claims description 8
229940079593 drug Drugs 0.000 claims description 8
229910052731 fluorine Inorganic materials 0.000 claims description 8
208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims description 8
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 7
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 7
125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 7
208000030507 AIDS Diseases 0.000 claims description 7
102000004274 CCR5 Receptors Human genes 0.000 claims description 7
108010017088 CCR5 Receptors Proteins 0.000 claims description 7
239000002585 base Substances 0.000 claims description 7
208000035475 disorder Diseases 0.000 claims description 7
125000005842 heteroatom Chemical group 0.000 claims description 7
229940124597 therapeutic agent Drugs 0.000 claims description 7
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 6
241001430294 unidentified retrovirus Species 0.000 claims description 6
241000124008 Mammalia Species 0.000 claims description 5
239000011737 fluorine Substances 0.000 claims description 5
229910052799 carbon Inorganic materials 0.000 claims description 4
239000003085 diluting agent Substances 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
239000000546 pharmaceutical excipient Substances 0.000 claims description 4
239000000825 pharmaceutical preparation Substances 0.000 claims description 4
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 3
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 3
125000003342 alkenyl group Chemical group 0.000 claims description 3
125000000304 alkynyl group Chemical group 0.000 claims description 3
125000003118 aryl group Chemical group 0.000 claims description 3
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
229910052757 nitrogen Inorganic materials 0.000 claims description 3
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 2
125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 2
125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000002947 alkylene group Chemical group 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
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238000002360 preparation method Methods 0.000 description 140
239000000243 solution Substances 0.000 description 131
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FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 15
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 15
241000725303 Human immunodeficiency virus Species 0.000 description 14
150000001412 amines Chemical class 0.000 description 14
239000012321 sodium triacetoxyborohydride Substances 0.000 description 13
150000001335 aliphatic alkanes Chemical class 0.000 description 12
VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 12
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229910000041 hydrogen chloride Inorganic materials 0.000 description 12
XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 12
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239000003419 rna directed dna polymerase inhibitor Substances 0.000 description 9
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102100035875 C-C chemokine receptor type 5 Human genes 0.000 description 8
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229940029284 trichlorofluoromethane Drugs 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
229910052722 tritium Inorganic materials 0.000 description 1
229940046728 tumor necrosis factor alpha inhibitor Drugs 0.000 description 1
239000002452 tumor necrosis factor alpha inhibitor Substances 0.000 description 1
102000003298 tumor necrosis factor receptor Human genes 0.000 description 1
229960002004 valdecoxib Drugs 0.000 description 1
LNPDTQAFDNKSHK-UHFFFAOYSA-N valdecoxib Chemical compound CC=1ON=C(C=2C=CC=CC=2)C=1C1=CC=C(S(N)(=O)=O)C=C1 LNPDTQAFDNKSHK-UHFFFAOYSA-N 0.000 description 1
229940099259 vaseline Drugs 0.000 description 1
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238000005550 wet granulation Methods 0.000 description 1
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229960000523 zalcitabine Drugs 0.000 description 1
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Classifications

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Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
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Public Health (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Diabetes (AREA)
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Biomedical Technology (AREA)
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Pulmonology (AREA)
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Communicable Diseases (AREA)
Virology (AREA)
Oncology (AREA)
Heart & Thoracic Surgery (AREA)
Hospice & Palliative Care (AREA)
Dermatology (AREA)
Obesity (AREA)
Endocrinology (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Pain & Pain Management (AREA)
Transplantation (AREA)
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HR20040940A 2002-04-08 2004-10-07 Tropane derivatives as ccr5 modulators HRP20040940A2 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
GBGB0208071.1A GB0208071D0 (en)	2002-04-08	2002-04-08	Tropane derivatives useful in therapy
GB0301575A GB0301575D0 (en)	2003-01-23	2003-01-23	Tropane derivatives useful in therapy
PCT/IB2003/001220 WO2003084954A1 (fr)	2002-04-08	2003-03-31	Derives de tropane utilises comme modulateur as de ccr5

Publications (1)

Publication Number	Publication Date
HRP20040940A2 true HRP20040940A2 (en)	2005-04-30

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ID=28793308

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HR20040940A HRP20040940A2 (en)	2002-04-08	2004-10-07	Tropane derivatives as ccr5 modulators

Country Status (41)

Country	Link
EP (1)	EP1492789B1 (fr)
JP (2)	JP3793200B2 (fr)
KR (1)	KR100734685B1 (fr)
CN (1)	CN1324025C (fr)
AP (1)	AP1789A (fr)
AR (1)	AR039383A1 (fr)
AT (1)	ATE328882T1 (fr)
AU (1)	AU2003214503B2 (fr)
BR (1)	BR0309118A (fr)
CA (1)	CA2481482C (fr)
CR (1)	CR7514A (fr)
CU (1)	CU23282A3 (fr)
CY (1)	CY1106114T1 (fr)
DE (1)	DE60305903T2 (fr)
DK (1)	DK1492789T3 (fr)
DO (1)	DOP2003000624A (fr)
EA (1)	EA007590B1 (fr)
ES (1)	ES2263960T3 (fr)
GE (1)	GEP20074210B (fr)
HK (1)	HK1076102A1 (fr)
HN (1)	HN2003000114A (fr)
HR (1)	HRP20040940A2 (fr)
IL (1)	IL164261A0 (fr)
IS (1)	IS2577B (fr)
MA (1)	MA27190A1 (fr)
MX (1)	MXPA04009220A (fr)
MY (1)	MY134223A (fr)
NI (1)	NI200300053A (fr)
NO (1)	NO329674B1 (fr)
NZ (1)	NZ535452A (fr)
OA (1)	OA12798A (fr)
PA (1)	PA8570801A1 (fr)
PE (1)	PE20040082A1 (fr)
PL (1)	PL372968A1 (fr)
PT (1)	PT1492789E (fr)
RS (1)	RS51550B (fr)
SI (1)	SI1492789T1 (fr)
TN (1)	TNSN04194A1 (fr)
TW (1)	TWI280130B (fr)
UY (1)	UY27752A1 (fr)
WO (1)	WO2003084954A1 (fr)

Families Citing this family (30)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6855724B2 (en)	2002-04-08	2005-02-15	Agouron Pharmaceuticals, Inc.	Tropane derivatives useful in therapy
WO2003084954A1 (fr) *	2002-04-08	2003-10-16	Pfizer Limited	Derives de tropane utilises comme modulateur as de ccr5
EP1786816A4 (fr)	2003-09-10	2009-11-04	Virochem Pharma Inc	Composes de spirohydantoine et procedes de modulation de l'activite des recepteurs de chimiokine
US7309790B2 (en) *	2003-10-03	2007-12-18	Pfizer Inc	Chemical compounds
TW200533348A (en)	2004-02-18	2005-10-16	Theravance Inc	Indazole-carboxamide compounds as 5-ht4 receptor agonists
US8131026B2 (en)	2004-04-16	2012-03-06	Validity Sensors, Inc.	Method and apparatus for fingerprint image reconstruction
WO2006041780A1 (fr)	2004-10-04	2006-04-20	Validity Sensors, Inc.	Groupes de detection d'empreintes digitales comprenant un substrat
WO2006064340A2 (fr) *	2004-12-13	2006-06-22	Pfizer Limited	Elaboration de n-acyl beta-aminoaldehydes
WO2008063600A2 (fr) *	2006-11-17	2008-05-29	Concert Pharmaceuticals Inc.	Dérivés de triazolyle tropane
DK2134712T3 (da) *	2007-04-13	2013-11-18	Dong Wha Pharm Co Ltd	Aspartat af 1-cyclopropyl-6-fluoro-7-(8-methoxyimino-2,6-diaza-spiro(3, 4)oct-6-yl)-4-oxo-1,4-dihydro-(1,8) naphthyridin-3-karboxylsyre, fremgangsmåde til fremstilling af samme og antimikrobielt farmaceutisk sammensætning omfattende samme
ATE502939T1 (de) *	2007-08-27	2011-04-15	Theravance Inc	Disubstituierte alkyl-8-azabicycloä3.2.1üoktan- verbindungen als mu-opioid-rezeptorantagonisten
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
CA2778206A1 (fr) *	2009-11-21	2011-05-26	F. Hoffmann-La Roche Ag	Composes antiviraux heterocycliques
UY33110A (es)	2009-12-23	2011-07-29	Ironwood Pharmaceuticals Inc	Moduladores de CRTH2
MX2012011415A (es)	2010-04-02	2013-02-26	Phivco 1 Llc	Terapia de combinacion que comprende un antagonista de ccr5, un inhibidor de proteasa de vih-1, y un potenciador farmacocinetico.
WO2012009134A1 (fr)	2010-07-12	2012-01-19	Ironwood Pharmaceuticals, Inc.	Modulateurs de crth2
WO2012009137A1 (fr)	2010-07-12	2012-01-19	Ironwood Pharmaceuticals, Inc.	Modulateurs de crth2
HUE047354T2 (hu)	2011-05-18	2020-04-28	Vertex Pharmaceuticals Europe Ltd	Ivacaftor deuterizált származékai
US20140271680A1 (en)	2011-08-12	2014-09-18	Universite Paris-Est Creteil Val De Marne	Methods and pharmaceutical compositions for treatment of pulmonary hypertension
CN103159754A (zh) *	2011-12-19	2013-06-19	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
JP6146990B2 (ja) *	2012-11-16	2017-06-14	コンサートファーマシューティカルズインコーポレイテッド	重水素化されたｃｆｔｒ増強物質
GB201321749D0 (en) *	2013-12-09	2014-01-22	Ucb Pharma Sa	Therapeutic agents
GB201321748D0 (en) *	2013-12-09	2014-01-22	Ucb Pharma Sa	Therapeutic agents
WO2016160945A1 (fr)	2015-03-31	2016-10-06	Concert Pharmaceuticals, Inc.	Vx-661 deutéré
MA42954A (fr)	2015-09-25	2018-08-01	Vertex Pharmaceuticals Europe Ltd	Potentialisateurs cftr deutérés
JP2017105824A (ja) *	2017-02-10	2017-06-15	コンサートファーマシューティカルズインコーポレイテッド	重水素化されたｃｆｔｒ増強物質
CN117924170A (zh)	2017-12-01	2024-04-26	弗特克斯药品有限公司	用于制备囊性纤维化跨膜传导调节因子的调节剂的方法
EP3768256A4 (fr)	2018-03-19	2021-11-24	Emory University	Inhibiteurs d'entrée pantropique
JP6654223B2 (ja) *	2018-08-13	2020-02-26	バーテックスファーマシューティカルズ（ヨーロッパ）リミテッド	重水素化されたｃｆｔｒ増強物質
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

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
PE20001420A1 (es) *	1998-12-23	2000-12-18	Pfizer	Moduladores de ccr5
WO2001080106A1 (fr) *	2000-04-19	2001-10-25	Satoshi Yamazaki	Procede de diffusion d'outil publicitaire et support magnetique pour le logiciel
KR100548854B1 (ko) *	2000-05-26	2006-02-02	화이자 인코포레이티드	Ｃｃｒ5 조절제로서의 트리아졸릴 트로판 유도체
WO2003084954A1 (fr) *	2002-04-08	2003-10-16	Pfizer Limited	Derives de tropane utilises comme modulateur as de ccr5

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- 2003-04-07 HN HN2003000114A patent/HN2003000114A/es unknown
- 2003-04-07 UY UY27752A patent/UY27752A1/es unknown
- 2003-04-08 PA PA20038570801A patent/PA8570801A1/es unknown
2004
- 2004-09-16 IS IS7453A patent/IS2577B/is unknown
- 2004-09-29 MA MA27883A patent/MA27190A1/fr unknown
- 2004-10-06 TN TNP2004000194A patent/TNSN04194A1/fr unknown
- 2004-10-07 CR CR7514A patent/CR7514A/es unknown
- 2004-10-07 CU CU20040219A patent/CU23282A3/es unknown
- 2004-10-07 HR HR20040940A patent/HRP20040940A2/hr not_active Application Discontinuation
- 2004-10-26 NO NO20044615A patent/NO329674B1/no not_active IP Right Cessation
2005
- 2005-09-16 HK HK05108146A patent/HK1076102A1/xx not_active IP Right Cessation
2006
- 2006-02-03 JP JP2006027537A patent/JP4571078B2/ja not_active Expired - Lifetime
- 2006-07-04 CY CY20061100919T patent/CY1106114T1/el unknown

Also Published As

Publication number	Publication date
CN1646526A (zh)	2005-07-27
HN2003000114A (es)	2004-05-05
PA8570801A1 (es)	2004-11-26
EA200401167A1 (ru)	2005-04-28
IS2577B (is)	2010-02-15
AR039383A1 (es)	2005-02-16
DOP2003000624A (es)	2003-10-15
BR0309118A (pt)	2005-02-01
DE60305903T2 (de)	2007-03-08
DK1492789T3 (da)	2006-09-11
JP2005532285A (ja)	2005-10-27
JP2006182784A (ja)	2006-07-13
MY134223A (en)	2007-11-30
NO329674B1 (no)	2010-11-29
RS88804A (en)	2006-12-15
MXPA04009220A (es)	2005-09-30
NZ535452A (en)	2006-11-30
TWI280130B (en)	2007-05-01
PT1492789E (pt)	2006-09-29
AU2003214503B2 (en)	2008-08-07
TW200403242A (en)	2004-03-01
NI200300053A (es)	2005-11-01
HK1076102A1 (en)	2006-01-06
PL372968A1 (en)	2005-08-08
CR7514A (es)	2004-11-08
ATE328882T1 (de)	2006-06-15
AP2004003147A0 (en)	2004-09-30
DE60305903D1 (de)	2006-07-20
CA2481482A1 (fr)	2003-10-16
RS51550B (en)	2011-06-30
IS7453A (is)	2004-09-16
JP3793200B2 (ja)	2006-07-05
CU23282A3 (es)	2008-06-30
WO2003084954A1 (fr)	2003-10-16
JP4571078B2 (ja)	2010-10-27
SI1492789T1 (sl)	2006-10-31
TNSN04194A1 (fr)	2007-03-12
CN1324025C (zh)	2007-07-04
EP1492789A1 (fr)	2005-01-05
NO20044615L (no)	2004-10-26
MA27190A1 (fr)	2005-01-03
AP1789A (en)	2007-10-05
EP1492789B1 (fr)	2006-06-07
AU2003214503A1 (en)	2003-10-20
ES2263960T3 (es)	2006-12-16
CA2481482C (fr)	2009-11-10
UY27752A1 (es)	2003-11-28
GEP20074210B (en)	2007-10-10
KR20040099420A (ko)	2004-11-26
OA12798A (en)	2006-07-10
KR100734685B1 (ko)	2007-07-02
EA007590B1 (ru)	2006-12-29
PE20040082A1 (es)	2004-03-20
CY1106114T1 (el)	2011-06-08
IL164261A0 (en)	2005-12-18

Legal Events

Date	Code	Title	Description
2005-04-30	A1OB	Publication of a patent application
2005-10-12	ARAI	Request for the grant of a patent on the basis of the submitted results of a substantive examination of a patent application
2011-03-21	ODRP	Renewal fee for the maintenance of a patent	Payment date: 20110321 Year of fee payment: 9
2012-10-09	OBST	Application withdrawn

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US7790740B2 (en)	2010-09-07	Imidazopyridine substituted tropane derivatives with CCR5 receptor antagonist activity for the treatment of HIV and inflammation
EP3286191B1 (fr)	2020-07-29	Nouvelles dihydropyridoisoquinolinones et leurs compositions pharmaceutiques pour le traitement de troubles inflammatoires
US7579471B2 (en)	2009-08-25	Tropane derivatives useful in therapy
NL1027301C2 (nl)	2005-09-20	Tropaanderivaten.
ZA200602096B (en)	2007-05-30	Imidazopyridine substituted tropane derivatives with CCR5 receptor antagonist activity for the treatment of HIV and inflammation