OA12118A - PyrroloÄ2,3-dÜpyrimidine compounds. - Google Patents

PyrroloÄ2,3-dÜpyrimidine compounds. Download PDF

Info

Publication number: OA12118A
Authority: OA; OAPI
Prior art keywords: alkyl; amino; methyl; cyano; compound according
Prior art date: 1999-12-10

Application number

OA1200200178A

Other languages

English (en)

Inventor

Todd Andrew Blumenkopf

Mark Edward Flanagan

Michael John Munchhof

Original Assignee

Pfizer Prod 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.)

1999-12-10

Filing date

2000-11-23

Publication date

2006-05-04

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=22618882&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=OA12118(A) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

2000-11-23 Application filed by Pfizer Prod Inc filed Critical Pfizer Prod Inc

2006-05-04 Publication of OA12118A publication Critical patent/OA12118A/en

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 119
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206010028980 Neoplasm Diseases 0.000 claims abstract description 8
201000004681 Psoriasis Diseases 0.000 claims abstract description 8
201000011510 cancer Diseases 0.000 claims abstract description 8
206010025135 lupus erythematosus Diseases 0.000 claims abstract description 8
208000024827 Alzheimer disease Diseases 0.000 claims abstract description 7
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208000032839 leukemia Diseases 0.000 claims abstract description 6
201000006417 multiple sclerosis Diseases 0.000 claims abstract description 6
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201000006704 Ulcerative Colitis Diseases 0.000 claims abstract description 5
229940121363 anti-inflammatory agent Drugs 0.000 claims abstract description 4
239000002260 anti-inflammatory agent Substances 0.000 claims abstract description 4
125000000217 alkyl group Chemical group 0.000 claims description 93
-1 hydroxy, amino Chemical group 0.000 claims description 63
108010019421 Janus Kinase 3 Proteins 0.000 claims description 25
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239000000203 mixture Substances 0.000 claims description 24
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 24
125000004093 cyano group Chemical group *C#N 0.000 claims description 20
125000003545 alkoxy group Chemical group 0.000 claims description 18
125000003282 alkyl amino group Chemical group 0.000 claims description 17
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 17
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 17
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 15
125000002252 acyl group Chemical group 0.000 claims description 14
YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 13
229910052805 deuterium Inorganic materials 0.000 claims description 13
229910052739 hydrogen Inorganic materials 0.000 claims description 13
239000001257 hydrogen Substances 0.000 claims description 13
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 12
125000004442 acylamino group Chemical group 0.000 claims description 12
239000003795 chemical substances by application Substances 0.000 claims description 12
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238000007792 addition Methods 0.000 claims description 10
208000035475 disorder Diseases 0.000 claims description 10
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UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 8
125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 8
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201000004624 Dermatitis Diseases 0.000 claims description 7
125000000304 alkynyl group Chemical group 0.000 claims description 7
125000003118 aryl group Chemical group 0.000 claims description 7
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125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
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QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
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125000004414 alkyl thio group Chemical group 0.000 claims description 2
125000001769 aryl amino group Chemical group 0.000 claims description 2
125000005135 aryl sulfinyl group Chemical group 0.000 claims description 2
125000005110 aryl thio group Chemical group 0.000 claims description 2
150000004702 methyl esters Chemical class 0.000 claims description 2
125000004043 oxo group Chemical group O=* 0.000 claims description 2
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
SGPGESCZOCHFCL-UHFFFAOYSA-N Tilisolol hydrochloride Chemical compound [Cl-].C1=CC=C2C(=O)N(C)C=C(OCC(O)C[NH2+]C(C)(C)C)C2=C1 SGPGESCZOCHFCL-UHFFFAOYSA-N 0.000 claims 13
125000001475 halogen functional group Chemical group 0.000 claims 6
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238000004519 manufacturing process Methods 0.000 claims 4
238000002689 xenotransplantation Methods 0.000 claims 2
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
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102220418944 c.46C>A Human genes 0.000 claims 1
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LRIZCRLAGSEHSM-UHFFFAOYSA-N n,n,4-trimethyl-3-[methyl(7h-pyrrolo[2,3-d]pyrimidin-4-yl)amino]piperidine-1-carboxamide Chemical compound CC1CCN(C(=O)N(C)C)CC1N(C)C1=NC=NC2=C1C=CN2 LRIZCRLAGSEHSM-UHFFFAOYSA-N 0.000 claims 1
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims 1
QUUYRYYUKNNNNS-UHFFFAOYSA-N piperidine-1-carboximidamide Chemical compound NC(=N)N1CCCCC1 QUUYRYYUKNNNNS-UHFFFAOYSA-N 0.000 claims 1
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238000000034 method Methods 0.000 description 22
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239000002585 base Substances 0.000 description 19
150000003839 salts Chemical class 0.000 description 17
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 14
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 14
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
239000002253 acid Substances 0.000 description 14
239000000243 solution Substances 0.000 description 11
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KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
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210000001744 T-lymphocyte Anatomy 0.000 description 8
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125000005843 halogen group Chemical group 0.000 description 8
PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 description 7
108010036949 Cyclosporine Proteins 0.000 description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 7
125000006239 protecting group Chemical group 0.000 description 7
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MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
150000007513 acids Chemical class 0.000 description 6
150000001768 cations Chemical class 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
239000003153 chemical reaction reagent Substances 0.000 description 5
239000000651 prodrug Substances 0.000 description 5
229940002612 prodrug Drugs 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
125000003601 C2-C6 alkynyl group Chemical group 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
QJJXYPPXXYFBGM-LFZNUXCKSA-N Tacrolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1\C=C(/C)[C@@H]1[C@H](C)[C@@H](O)CC(=O)[C@H](CC=C)/C=C(C)/C[C@H](C)C[C@H](OC)[C@H]([C@H](C[C@H]2C)OC)O[C@@]2(O)C(=O)C(=O)N2CCCC[C@H]2C(=O)O1 QJJXYPPXXYFBGM-LFZNUXCKSA-N 0.000 description 4
150000001408 amides Chemical class 0.000 description 4
LMEKQMALGUDUQG-UHFFFAOYSA-N azathioprine Chemical compound CN1C=NC([N+]([O-])=O)=C1SC1=NC=NC2=C1NC=N2 LMEKQMALGUDUQG-UHFFFAOYSA-N 0.000 description 4
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BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
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GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
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QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
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NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 2
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QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical class CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
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UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
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150000004943 pyrrolo[2,3-d]pyrimidines Chemical class 0.000 description 1
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102200025788 rs179363875 Human genes 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
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239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
235000017550 sodium carbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
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239000008109 sodium starch glycolate Substances 0.000 description 1
229920003109 sodium starch glycolate Polymers 0.000 description 1
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239000000758 substrate Substances 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
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QJJXYPPXXYFBGM-SHYZHZOCSA-N tacrolimus Natural products CO[C@H]1C[C@H](CC[C@@H]1O)C=C(C)[C@H]2OC(=O)[C@H]3CCCCN3C(=O)C(=O)[C@@]4(O)O[C@@H]([C@H](C[C@H]4C)OC)[C@@H](C[C@H](C)CC(=C[C@@H](CC=C)C(=O)C[C@H](O)[C@H]2C)C)OC QJJXYPPXXYFBGM-SHYZHZOCSA-N 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
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125000005306 thianaphthenyl group Chemical group 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
125000004568 thiomorpholinyl group Chemical group 0.000 description 1
229940104230 thymidine Drugs 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
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150000003668 tyrosines Chemical class 0.000 description 1
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Classifications

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Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
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General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
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Pharmacology & Pharmacy (AREA)
Organic Chemistry (AREA)
Epidemiology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Immunology (AREA)
Diabetes (AREA)
Neurosurgery (AREA)
Rheumatology (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Gastroenterology & Hepatology (AREA)
Pulmonology (AREA)
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Neurology (AREA)
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Psychiatry (AREA)
Emergency Medicine (AREA)
Oncology (AREA)
Orthopedic Medicine & Surgery (AREA)
Physical Education & Sports Medicine (AREA)
Obesity (AREA)
Transplantation (AREA)
Endocrinology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

OA1200200178A 1999-12-10 2000-11-23 PyrroloÄ2,3-dÜpyrimidine compounds. OA12118A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US17017999P	1999-12-10	1999-12-10

Publications (1)

Publication Number	Publication Date
OA12118A true OA12118A (en)	2006-05-04

Family

ID=22618882

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA1200200178A OA12118A (en)	1999-12-10	2000-11-23	PyrroloÄ2,3-dÜpyrimidine compounds.

Country Status (53)

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WO (1)	WO2001042246A2 (is)
ZA (1)	ZA200204535B (is)

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Publication number	Publication date
AU1295001A (en)	2001-06-18
MY130760A (en)	2007-07-31
NO20022738D0 (no)	2002-06-07
YU41302A (sh)	2005-03-15
US20070292430A1 (en)	2007-12-20
RS51574B (sr)	2011-08-31
US7091208B2 (en)	2006-08-15
SI1235830T1 (en)	2004-06-30
SV2002000236A (es)	2002-06-07
GEP20053479B (en)	2005-03-25
UY26477A1 (es)	2001-06-29
US7601727B2 (en)	2009-10-13
AP1905A (en)	2008-10-20
US7265221B2 (en)	2007-09-04
CN1195755C (zh)	2005-04-06
US20050288313A1 (en)	2005-12-29
IL149616A0 (en)	2002-11-10
EE200200304A (et)	2003-06-16
PA8507301A1 (es)	2002-02-21
CZ303875B6 (cs)	2013-06-05
TNSN00239A1 (fr)	2005-11-10
PL355907A1 (en)	2004-05-31
ATE380031T1 (de)	2007-12-15
BRPI0016263B1 (pt)	2016-07-26
ES2208433T3 (es)	2004-06-16
HK1051195A1 (en)	2003-07-25
KR100477818B1 (ko)	2005-03-22
PT1235830E (pt)	2004-04-30
DE60007552D1 (de)	2004-02-05
CA2393640A1 (en)	2001-06-14
DZ3248A1 (fr)	2001-06-14
GT200000208A (es)	2002-06-01
CY1108850T1 (el)	2014-07-02
MXPA02005675A (es)	2002-09-02
DE60007552T2 (de)	2004-09-23
TWI248935B (en)	2006-02-11
HRP20020509B1 (en)	2005-06-30
WO2001042246A3 (en)	2001-11-22
US20040053947A1 (en)	2004-03-18
BRPI0016263B8 (pt)	2021-05-25
HUP0203503A3 (en)	2004-12-28
CN1409712A (zh)	2003-04-09
PL218519B1 (pl)	2014-12-31
TWI264305B (en)	2006-10-21
CA2393640C (en)	2006-09-05
NZ528905A (en)	2005-03-24
BG106855A (bg)	2002-12-29
NZ518884A (en)	2004-02-27
US20060241131A1 (en)	2006-10-26
US6627754B2 (en)	2003-09-30
EE05351B1 (et)	2010-10-15
IS6383A (is)	2002-05-14
EA006227B1 (ru)	2005-10-27
KR20020061637A (ko)	2002-07-24
PT1382339E (pt)	2008-02-06
US7842699B2 (en)	2010-11-30
NO323378B1 (no)	2007-04-16
HUP0203503A2 (hu)	2003-02-28
JP4078074B2 (ja)	2008-04-23
US6956041B2 (en)	2005-10-18
TR200400105T4 (tr)	2004-02-23
IS2173B (is)	2006-11-15
EP1235830A2 (en)	2002-09-04
CU23220A3 (es)	2007-07-20
CO5271665A1 (es)	2003-04-30
PE20011096A1 (es)	2001-10-25
IL149616A (en)	2010-02-17
EP1382339B1 (en)	2007-12-05
DK1382339T3 (da)	2008-01-28
ES2295495T3 (es)	2008-04-16
AU777911B2 (en)	2004-11-04
ECSP003819A (es)	2001-06-11
EA200200506A1 (ru)	2002-12-26
EP1235830B1 (en)	2004-01-02
HN2000000265A (es)	2001-04-11
MA26851A1 (fr)	2004-12-20
DE60037345T2 (de)	2008-11-13
USRE41783E1 (en)	2010-09-28
TR200201498T2 (tr)	2003-01-21
HU229671B1 (en)	2014-04-28
CR6655A (es)	2003-11-07
AR026534A1 (es)	2003-02-12
WO2001042246A2 (en)	2001-06-14
BR0016263A (pt)	2002-08-13
EP1382339A1 (en)	2004-01-21
EG24399A (en)	2009-04-29
NO20022738L (no)	2002-06-07
TW200427453A (en)	2004-12-16
BG65821B1 (bg)	2010-01-29
SK287188B6 (sk)	2010-02-08
US20010053782A1 (en)	2001-12-20
AP2002002543A0 (en)	2002-06-30
DK1235830T3 (da)	2004-03-29
JP2003516405A (ja)	2003-05-13
ZA200204535B (en)	2003-09-29
US20100035903A1 (en)	2010-02-11
UA72290C2 (uk)	2005-02-15
CZ20021846A3 (cs)	2003-06-18
SK7562002A3 (en)	2003-08-05
ATE257157T1 (de)	2004-01-15
DE60037345D1 (de)	2008-01-17
HRP20020509A2 (en)	2004-08-31

Publication	Publication Date	Title
US6627754B2 (en)	2003-09-30	Pyrrolo[2,3-d]pyrimidine compounds
US7250420B2 (en)	2007-07-31	Method of treatment of transplant rejection
EP1666481B1 (en)	2012-09-19	3-((3R,4R)-4-Methyl-3-[methyl-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-amino]-piperidinyl)-3-oxo-propionitrile as protein kinase inhibitor
CA2545192A1 (en)	2005-06-09	Method of treatment of atherosclerosis
CA2549485A1 (en)	2005-07-07	Pyrrolo [2,3-d] pyrimidine compounds for treating transplant rejection
NZ522364A (en)	2004-09-24	Pyrrolo[2,3-d]pyrimidine compounds as immunosuppressive agents