NO329674B1 - Tropanderivater, farmasoytiske sammensetninger og anvendelser - Google Patents

Tropanderivater, farmasoytiske sammensetninger og anvendelser Download PDF

Info

Publication number: NO329674B1
Authority: NO; Norway
Prior art keywords: alkyl; mmol; formula; methyl; dichloromethane
Prior art date: 2002-04-08

Application number

NO20044615A

Other languages

English (en)

Norwegian (no)

Other versions

NO20044615L (no

Inventor

Anthony Wood

Patricia Ann Basford

Peter Thomas Stephenson

Stefan Colin John Taylor

Original Assignee

Pfizer

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

2004-10-26

Publication date

2010-11-29

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

2004-10-26 Application filed by Pfizer filed Critical Pfizer

2004-10-26 Publication of NO20044615L publication Critical patent/NO20044615L/no

2010-11-29 Publication of NO329674B1 publication Critical patent/NO329674B1/no

Links

239000008194 pharmaceutical composition Substances 0.000 title claims description 6
150000003813 tropane derivatives Chemical class 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 286
238000011282 treatment Methods 0.000 claims abstract description 36
102000004274 CCR5 Receptors Human genes 0.000 claims abstract description 11
108010017088 CCR5 Receptors Proteins 0.000 claims abstract description 11
208000027866 inflammatory disease Diseases 0.000 claims abstract description 8
125000000217 alkyl group Chemical group 0.000 claims description 56
150000003839 salts Chemical class 0.000 claims description 50
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 42
239000012453 solvate Substances 0.000 claims description 39
-1 mono-fluoro-substituted phenyl Chemical group 0.000 claims description 34
125000001153 fluoro group Chemical group F* 0.000 claims description 25
239000003814 drug Substances 0.000 claims description 24
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
125000004429 atom Chemical group 0.000 claims description 8
201000010099 disease Diseases 0.000 claims description 8
229910052736 halogen Inorganic materials 0.000 claims description 7
150000002367 halogens Chemical class 0.000 claims description 7
125000006239 protecting group Chemical group 0.000 claims description 7
208000030507 AIDS Diseases 0.000 claims description 6
125000000753 cycloalkyl group Chemical group 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 6
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
206010038997 Retroviral infections Diseases 0.000 claims description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 5
239000000546 pharmaceutical excipient Substances 0.000 claims description 5
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 5
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
239000003085 diluting agent Substances 0.000 claims description 4
229910052731 fluorine Inorganic materials 0.000 claims description 4
125000002947 alkylene group Chemical group 0.000 claims description 3
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 2
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 2
125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
239000000969 carrier Substances 0.000 claims 1
102000019034 Chemokines Human genes 0.000 abstract description 10
108010012236 Chemokines Proteins 0.000 abstract description 10
230000000694 effects Effects 0.000 abstract description 6
208000015181 infectious disease Diseases 0.000 abstract description 6
239000005557 antagonist Substances 0.000 abstract description 3
241001430294 unidentified retrovirus Species 0.000 abstract description 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 513
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 192
239000000243 solution Substances 0.000 description 162
238000002360 preparation method Methods 0.000 description 141
239000002904 solvent Substances 0.000 description 134
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 120
230000002829 reductive effect Effects 0.000 description 120
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 102
239000011541 reaction mixture Substances 0.000 description 87
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 81
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 72
239000000203 mixture Substances 0.000 description 71
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 71
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 60
229910001868 water Inorganic materials 0.000 description 59
229910052757 nitrogen Inorganic materials 0.000 description 51
239000006260 foam Substances 0.000 description 49
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 48
239000000741 silica gel Substances 0.000 description 48
229910002027 silica gel Inorganic materials 0.000 description 48
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 48
239000000047 product Substances 0.000 description 47
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 43
238000003818 flash chromatography Methods 0.000 description 43
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 42
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 42
238000000034 method Methods 0.000 description 41
229920006395 saturated elastomer Polymers 0.000 description 40
238000005481 NMR spectroscopy Methods 0.000 description 39
239000012074 organic phase Substances 0.000 description 39
229910000030 sodium bicarbonate Inorganic materials 0.000 description 35
235000017557 sodium bicarbonate Nutrition 0.000 description 35
239000007787 solid Substances 0.000 description 35
238000006243 chemical reaction Methods 0.000 description 33
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
238000005160 1H NMR spectroscopy Methods 0.000 description 29
DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 29
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 28
239000010410 layer Substances 0.000 description 22
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 22
239000002253 acid Substances 0.000 description 20
239000012044 organic layer Substances 0.000 description 19
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 18
241000725303 Human immunodeficiency virus Species 0.000 description 17
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 17
239000011734 sodium Substances 0.000 description 17
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 16
229960000583 acetic acid Drugs 0.000 description 16
239000008346 aqueous phase Substances 0.000 description 16
239000000284 extract Substances 0.000 description 16
150000001412 amines Chemical class 0.000 description 14
239000000543 intermediate Substances 0.000 description 14
239000012321 sodium triacetoxyborohydride Substances 0.000 description 13
VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 12
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 12
229910000041 hydrogen chloride Inorganic materials 0.000 description 12
FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 11
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 11
150000001350 alkyl halides Chemical class 0.000 description 11
229940079593 drug Drugs 0.000 description 11
239000007789 gas Substances 0.000 description 11
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 10
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 10
239000012346 acetyl chloride Substances 0.000 description 10
229910052739 hydrogen Inorganic materials 0.000 description 10
XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 10
YNTOKMNHRPSGFU-UHFFFAOYSA-N n-Propyl carbamate Chemical compound CCCOC(N)=O YNTOKMNHRPSGFU-UHFFFAOYSA-N 0.000 description 10
239000003921 oil Substances 0.000 description 10
238000010992 reflux Methods 0.000 description 10
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 10
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
102100035875 C-C chemokine receptor type 5 Human genes 0.000 description 9
101710149870 C-C chemokine receptor type 5 Proteins 0.000 description 9
230000000875 corresponding effect Effects 0.000 description 9
239000003112 inhibitor Substances 0.000 description 9
239000012267 brine Substances 0.000 description 8
239000001257 hydrogen Substances 0.000 description 8
229910052943 magnesium sulfate Inorganic materials 0.000 description 8
235000019341 magnesium sulphate Nutrition 0.000 description 8
NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 8
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
101150041968 CDC13 gene Proteins 0.000 description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 7
239000000706 filtrate Substances 0.000 description 7
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102000005962 receptors Human genes 0.000 description 7
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230000009467 reduction Effects 0.000 description 7
238000006722 reduction reaction Methods 0.000 description 7
MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 6
KSNKQSPJFRQSEI-UHFFFAOYSA-N 3,3,3-trifluoropropanoic acid Chemical compound OC(=O)CC(F)(F)F KSNKQSPJFRQSEI-UHFFFAOYSA-N 0.000 description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
206010001052 Acute respiratory distress syndrome Diseases 0.000 description 6
229920000858 Cyclodextrin Polymers 0.000 description 6
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 6
208000031886 HIV Infections Diseases 0.000 description 6
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YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
238000004458 analytical method Methods 0.000 description 6
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239000012362 glacial acetic acid Substances 0.000 description 6
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JFWMYCVMQSLLOO-UHFFFAOYSA-N cyclobutanecarbonyl chloride Chemical compound ClC(=O)C1CCC1 JFWMYCVMQSLLOO-UHFFFAOYSA-N 0.000 description 5
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239000000843 powder Substances 0.000 description 4
HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 4
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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 3
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LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 description 2
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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
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NO20044615A 2002-04-08 2004-10-26 Tropanderivater, farmasoytiske sammensetninger og anvendelser NO329674B1 (no)

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 (2)

Publication Number	Publication Date
NO20044615L NO20044615L (no)	2004-10-26
NO329674B1 true NO329674B1 (no)	2010-11-29

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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)
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)

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EP1492789B1 (fr) *	2002-04-08	2006-06-07	Pfizer Limited	Derives de tropane utilises comme modulateur de ccr5
US6855724B2 (en)	2002-04-08	2005-02-15	Agouron Pharmaceuticals, Inc.	Tropane derivatives useful in therapy
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
EP1682545B1 (fr) *	2003-10-03	2007-12-12	Pfizer Limited	Derives de tropane a substitution imidazopyridine en tant qu'antagonistes des recepteurs ccr5 pour le traitement du vih et de l'inflammation
GB0323236D0 (en) *	2003-10-03	2003-11-05	Pfizer Ltd	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
EP1800243B1 (fr)	2004-10-04	2010-08-11	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
AU2008239966C1 (en) *	2007-04-13	2012-03-29	Dong Wha Pharmaceutical Co., Ltd.	Aspartate of 1-cyclopropyl-6-fluoro-7-(8-methoxyimino-2,6-diaza- spiro[3.4]oct-6-yl)-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid, method for preparing the same, and antimicrobial pharmaceutical composition comprising the same
US7947710B2 (en)	2007-08-27	2011-05-24	Theravance, Inc.	Disubstituted alkyl-8-azabicyclo[3.2.1]octane compounds as mu opioid receptor antagonists
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
WO2011061243A1 (fr) *	2009-11-21	2011-05-26	F. Hoffmann-La Roche Ag	Composés antiviraux hétérocycliques
SG181900A1 (en)	2009-12-23	2012-08-30	Ironwood Pharmaceuticals Inc	Crth2 modulators
EP2552429A1 (fr)	2010-04-02	2013-02-06	Phivco-1 LLC	Traitement d'association comprenant un antagoniste du récepteur ccr5, un inhibiteur de la protéase du vih-1 et un accélérateur pharmacocinétique
US20130216552A1 (en)	2010-07-12	2013-08-22	Ironwood Pharmaceuticals, Inc.	Crth2 modulators
WO2012009134A1 (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
EP2741777B1 (fr)	2011-08-12	2017-01-18	INSERM - Institut National de la Santé et de la Recherche Médicale	Procédés et compositions pharmaceutiques pour le traitement de l'hypertension pulmonaire
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
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
EP3277647A1 (fr)	2015-03-31	2018-02-07	Vertex Pharmaceuticals (Europe) Limited	Vx-661 deutéré
EP3352758A2 (fr)	2015-09-25	2018-08-01	Vertex Pharmaceuticals (Europe) Limited	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
MA51206A (fr)	2017-12-01	2020-10-07	Vertex Pharma	Procédés pour préparer des modulateurs de régulateur de conductance transmembranaire de mucoviscidose
US11649235B2 (en)	2018-03-19	2023-05-16	Emory University	Pan-tropic entry inhibitors
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
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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
RS50904B (sr) *	2000-05-26	2010-08-31	Pfizer Inc.	Derivati tropana i njihova primena
EP1492789B1 (fr) *	2002-04-08	2006-06-07	Pfizer Limited	Derives de tropane utilises comme modulateur de ccr5

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Publication number	Publication date
AP2004003147A0 (en)	2004-09-30
EA007590B1 (ru)	2006-12-29
WO2003084954A1 (fr)	2003-10-16
AP1789A (en)	2007-10-05
KR20040099420A (ko)	2004-11-26
BR0309118A (pt)	2005-02-01
PL372968A1 (en)	2005-08-08
IS7453A (is)	2004-09-16
MA27190A1 (fr)	2005-01-03
HRP20040940A2 (en)	2005-04-30
CR7514A (es)	2004-11-08
PT1492789E (pt)	2006-09-29
SI1492789T1 (sl)	2006-10-31
EP1492789B1 (fr)	2006-06-07
CA2481482A1 (fr)	2003-10-16
ATE328882T1 (de)	2006-06-15
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