OA11572A - PyrroloÄ2,3-düpyrimidine compounds. - Google Patents

PyrroloÄ2,3-düpyrimidine compounds. Download PDF

Info

Publication number: OA11572A
Authority: OA; OAPI
Prior art keywords: alkyl; pyrrolo; methyl; pyrimidin; amino
Prior art date: 1998-06-19

Application number

OA1200000349A

Other languages

English (en)

Inventor

Todd Andrew Blumenkopf

Matthew Frank Brown

Paul Steven Changelian

Mark Edward Flanagan

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.)

1998-06-19

Filing date

1999-06-14

Publication date

2004-07-01

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=26781018&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=OA11572(A) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1999-06-14 Application filed by Pfizer Prod Inc filed Critical Pfizer Prod Inc

2004-07-01 Publication of OA11572A publication Critical patent/OA11572A/en

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 102
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206010039073 rheumatoid arthritis Diseases 0.000 claims abstract description 11
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206010028980 Neoplasm Diseases 0.000 claims abstract description 10
201000004681 Psoriasis Diseases 0.000 claims abstract description 10
208000024799 Thyroid disease Diseases 0.000 claims abstract description 10
201000006704 Ulcerative Colitis Diseases 0.000 claims abstract description 10
230000001363 autoimmune Effects 0.000 claims abstract description 10
201000011510 cancer Diseases 0.000 claims abstract description 10
208000032839 leukemia Diseases 0.000 claims abstract description 10
206010025135 lupus erythematosus Diseases 0.000 claims abstract description 10
208000023275 Autoimmune disease Diseases 0.000 claims abstract description 9
208000011231 Crohn disease Diseases 0.000 claims abstract description 9
102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims abstract description 9
108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims abstract description 9
201000006417 multiple sclerosis Diseases 0.000 claims abstract description 9
210000000056 organ Anatomy 0.000 claims abstract description 9
208000024827 Alzheimer disease Diseases 0.000 claims abstract description 7
125000000217 alkyl group Chemical group 0.000 claims description 176
-1 hydroxy, amino Chemical group 0.000 claims description 76
108010019421 Janus Kinase 3 Proteins 0.000 claims description 30
102000006500 Janus Kinase 3 Human genes 0.000 claims description 30
125000003545 alkoxy group Chemical group 0.000 claims description 29
125000001072 heteroaryl group Chemical group 0.000 claims description 27
125000000041 C6-C10 aryl group Chemical group 0.000 claims description 24
229910052739 hydrogen Inorganic materials 0.000 claims description 23
239000001257 hydrogen Substances 0.000 claims description 23
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 23
125000002252 acyl group Chemical group 0.000 claims description 21
125000004442 acylamino group Chemical group 0.000 claims description 20
125000000753 cycloalkyl group Chemical group 0.000 claims description 20
125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 19
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 18
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 17
125000003282 alkyl amino group Chemical group 0.000 claims description 17
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 15
241000124008 Mammalia Species 0.000 claims description 15
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
208000035475 disorder Diseases 0.000 claims description 13
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 13
125000004423 acyloxy group Chemical group 0.000 claims description 12
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 11
239000003795 chemical substances by application Substances 0.000 claims description 11
150000002431 hydrogen Chemical class 0.000 claims description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 9
YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 8
206010052779 Transplant rejections Diseases 0.000 claims description 8
125000000304 alkynyl group Chemical group 0.000 claims description 8
229910052805 deuterium Inorganic materials 0.000 claims description 8
206010003645 Atopy Diseases 0.000 claims description 7
201000004624 Dermatitis Diseases 0.000 claims description 7
125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 6
125000003342 alkenyl group Chemical group 0.000 claims description 6
230000005764 inhibitory process Effects 0.000 claims description 6
229940121363 anti-inflammatory agent Drugs 0.000 claims description 5
239000002260 anti-inflammatory agent Substances 0.000 claims description 5
239000003937 drug carrier Substances 0.000 claims description 5
239000008194 pharmaceutical composition Substances 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
210000000987 immune system Anatomy 0.000 claims description 4
125000000000 cycloalkoxy group Chemical group 0.000 claims description 3
108091000080 Phosphotransferase Proteins 0.000 claims description 2
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102200031660 rs730880032 Human genes 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims 4
125000001475 halogen functional group Chemical group 0.000 claims 3
QJLJAWHLBAUMAA-UHFFFAOYSA-N 2-[1-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)azetidin-3-yl]propan-2-ol Chemical compound C1C(C(C)(O)C)CN1C1=NC=NC2=C1C=CN2 QJLJAWHLBAUMAA-UHFFFAOYSA-N 0.000 claims 1
ZRJHSCQQVJJAFE-UHFFFAOYSA-N 2-[4-methyl-3-[methyl(7h-pyrrolo[2,3-d]pyrimidin-4-yl)amino]cyclohexyl]propan-2-ol Chemical compound CC1CCC(C(C)(C)O)CC1N(C)C1=NC=NC2=C1C=CN2 ZRJHSCQQVJJAFE-UHFFFAOYSA-N 0.000 claims 1
FACYDAGCXBRLET-UHFFFAOYSA-N 2-[4-methyl-5-[methyl(7h-pyrrolo[2,3-d]pyrimidin-4-yl)amino]cyclohex-3-en-1-yl]propan-2-ol Chemical compound N=1C=NC=2NC=CC=2C=1N(C)C1CC(C(C)(C)O)CC=C1C FACYDAGCXBRLET-UHFFFAOYSA-N 0.000 claims 1
201000010099 disease Diseases 0.000 claims 1
ZHMNGSTXFYRERK-UHFFFAOYSA-N n-(2-ethyl-4-prop-1-en-2-ylcyclopentyl)-n-methyl-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound CCC1CC(C(C)=C)CC1N(C)C1=NC=NC2=C1C=CN2 ZHMNGSTXFYRERK-UHFFFAOYSA-N 0.000 claims 1
239000003018 immunosuppressive agent Substances 0.000 abstract description 5
229940125721 immunosuppressive agent Drugs 0.000 abstract description 2
239000003112 inhibitor Substances 0.000 abstract description 2
238000002560 therapeutic procedure Methods 0.000 abstract description 2
206010012438 Dermatitis atopic Diseases 0.000 abstract 1
102000015617 Janus Kinases Human genes 0.000 abstract 1
108010024121 Janus Kinases Proteins 0.000 abstract 1
206010067584 Type 1 diabetes mellitus Diseases 0.000 abstract 1
201000008937 atopic dermatitis Diseases 0.000 abstract 1
206010012601 diabetes mellitus Diseases 0.000 abstract 1
238000000034 method Methods 0.000 description 63
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 49
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 40
239000000203 mixture Substances 0.000 description 40
239000000243 solution Substances 0.000 description 38
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 28
238000006243 chemical reaction Methods 0.000 description 27
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 23
238000002844 melting Methods 0.000 description 22
230000008018 melting Effects 0.000 description 22
150000003839 salts Chemical class 0.000 description 22
125000003118 aryl group Chemical group 0.000 description 21
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 20
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
239000011541 reaction mixture Substances 0.000 description 18
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 17
239000002585 base Substances 0.000 description 17
239000000047 product Substances 0.000 description 17
229940093499 ethyl acetate Drugs 0.000 description 15
235000019439 ethyl acetate Nutrition 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
210000004027 cell Anatomy 0.000 description 14
239000007787 solid Substances 0.000 description 14
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Natural products CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
125000005843 halogen group Chemical group 0.000 description 11
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 10
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
239000002253 acid Substances 0.000 description 9
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 9
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 9
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 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 8
108010036949 Cyclosporine Proteins 0.000 description 8
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 8
125000004093 cyano group Chemical group *C#N 0.000 description 8
238000010992 reflux Methods 0.000 description 8
125000004414 alkyl thio group Chemical group 0.000 description 7
239000003153 chemical reaction reagent Substances 0.000 description 7
238000001816 cooling Methods 0.000 description 7
239000002904 solvent Substances 0.000 description 7
125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
XTUVJUMINZSXGF-UHFFFAOYSA-N N-methylcyclohexylamine Chemical compound CNC1CCCCC1 XTUVJUMINZSXGF-UHFFFAOYSA-N 0.000 description 6
125000004391 aryl sulfonyl group Chemical group 0.000 description 6
125000005110 aryl thio group Chemical group 0.000 description 6
239000012267 brine Substances 0.000 description 6
150000001768 cations Chemical class 0.000 description 6
239000012043 crude product Substances 0.000 description 6
LTVOKYUPTHZZQH-UHFFFAOYSA-N difluoromethane Chemical group F[C]F LTVOKYUPTHZZQH-UHFFFAOYSA-N 0.000 description 6
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 6
BPTCCCTWWAUJRK-UHFFFAOYSA-N 4-chloro-7h-pyrrolo[2,3-d]pyrimidine Chemical compound ClC1=NC=NC2=C1C=CN2 BPTCCCTWWAUJRK-UHFFFAOYSA-N 0.000 description 5
102000004388 Interleukin-4 Human genes 0.000 description 5
108090000978 Interleukin-4 Proteins 0.000 description 5
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 5
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
210000001744 T-lymphocyte Anatomy 0.000 description 5
125000004390 alkyl sulfonyl group Chemical group 0.000 description 5
150000001412 amines Chemical class 0.000 description 5
125000005135 aryl sulfinyl group Chemical group 0.000 description 5
230000003197 catalytic effect Effects 0.000 description 5
235000019441 ethanol Nutrition 0.000 description 5
229910052943 magnesium sulfate Inorganic materials 0.000 description 5
235000019341 magnesium sulphate Nutrition 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
125000004193 piperazinyl group Chemical group 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
239000012312 sodium hydride Substances 0.000 description 5
229910000104 sodium hydride Inorganic materials 0.000 description 5
125000006528 (C2-C6) alkyl group Chemical group 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
PAFZNILMFXTMIY-UHFFFAOYSA-N Cyclohexylamine Natural products NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 4
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 4
LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 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
150000007513 acids Chemical class 0.000 description 4
239000003513 alkali Substances 0.000 description 4
125000004453 alkoxycarbonyl group Chemical group 0.000 description 4
125000004644 alkyl sulfinyl group Chemical group 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
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
238000001914 filtration Methods 0.000 description 4
238000009472 formulation Methods 0.000 description 4
HPNSFSBZBAHARI-UHFFFAOYSA-N micophenolic acid Natural products OC1=C(CC=C(C)CCC(O)=O)C(OC)=C(C)C2=C1C(=O)OC2 HPNSFSBZBAHARI-UHFFFAOYSA-N 0.000 description 4
231100000252 nontoxic Toxicity 0.000 description 4
230000003000 nontoxic effect Effects 0.000 description 4
229910052763 palladium Inorganic materials 0.000 description 4
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
238000010898 silica gel chromatography Methods 0.000 description 4
239000011734 sodium Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
125000004890 (C1-C6) alkylamino group Chemical group 0.000 description 3
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
229930105110 Cyclosporin A Natural products 0.000 description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
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 3
108060001084 Luciferase Proteins 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
125000004656 alkyl sulfonylamino group Chemical group 0.000 description 3
238000003556 assay Methods 0.000 description 3
SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 3
229940077388 benzenesulfonate Drugs 0.000 description 3
CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
125000001246 bromo group Chemical group Br* 0.000 description 3
239000002775 capsule Substances 0.000 description 3
229960001265 ciclosporin Drugs 0.000 description 3
230000008878 coupling Effects 0.000 description 3
238000010168 coupling process Methods 0.000 description 3
238000005859 coupling reaction Methods 0.000 description 3
125000004122 cyclic group Chemical group 0.000 description 3
229940043279 diisopropylamine Drugs 0.000 description 3
238000010790 dilution Methods 0.000 description 3
239000012895 dilution Substances 0.000 description 3
239000002552 dosage form Substances 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
229910052731 fluorine Inorganic materials 0.000 description 3
238000005227 gel permeation chromatography Methods 0.000 description 3
230000001506 immunosuppresive effect Effects 0.000 description 3
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230000001861 immunosuppressant effect Effects 0.000 description 3
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150000007524 organic acids Chemical class 0.000 description 3
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125000005936 piperidyl group Chemical group 0.000 description 3
229910052700 potassium Inorganic materials 0.000 description 3
235000011118 potassium hydroxide Nutrition 0.000 description 3
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QFJCIRLUMZQUOT-HPLJOQBZSA-N sirolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 QFJCIRLUMZQUOT-HPLJOQBZSA-N 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000011592 zinc chloride Substances 0.000 description 3
235000005074 zinc chloride Nutrition 0.000 description 3
125000006273 (C1-C3) alkyl group Chemical group 0.000 description 2
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
HFHPBMVMXFZJNO-UHFFFAOYSA-N 1-(cyclohexylamino)propan-2-ol Chemical compound CC(O)CNC1CCCCC1 HFHPBMVMXFZJNO-UHFFFAOYSA-N 0.000 description 2
MQWCXKGKQLNYQG-UHFFFAOYSA-N 4-methylcyclohexan-1-ol Chemical compound CC1CCC(O)CC1 MQWCXKGKQLNYQG-UHFFFAOYSA-N 0.000 description 2
ZYUZIQCTDGCTPB-UHFFFAOYSA-N 5-chloro-4-piperidin-1-yl-7h-pyrrolo[2,3-d]pyrimidine Chemical compound C=12C(Cl)=CNC2=NC=NC=1N1CCCCC1 ZYUZIQCTDGCTPB-UHFFFAOYSA-N 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
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ICMSIBMHHMSMHL-UHFFFAOYSA-N tert-butyl n-[2-[cycloheptyl(7h-pyrrolo[2,3-d]pyrimidin-4-yl)amino]ethyl]carbamate Chemical compound N=1C=NC=2NC=CC=2C=1N(CCNC(=O)OC(C)(C)C)C1CCCCCC1 ICMSIBMHHMSMHL-UHFFFAOYSA-N 0.000 description 1
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JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
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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
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- 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
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Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Immunology (AREA)
Diabetes (AREA)
Dermatology (AREA)
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OA1200000349A 1998-06-19 1999-06-14 PyrroloÄ2,3-düpyrimidine compounds. OA11572A (en)

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US8986698P	1998-06-19	1998-06-19
US10478798P	1998-10-19	1998-10-19

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1999
- 1999-06-14 EP EP99922454A patent/EP1087970B1/de not_active Expired - Lifetime
- 1999-06-14 IL IL13958699A patent/IL139586A0/xx active Protection Beyond IP Right Term
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- 1999-06-14 DK DK99922454T patent/DK1087970T3/da active
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- 1999-06-14 HU HU0102574A patent/HUP0102574A3/hu unknown
- 1999-06-14 WO PCT/IB1999/001100 patent/WO1999065908A1/en not_active Ceased
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- 1999-06-14 DE DE69916833T patent/DE69916833T2/de not_active Expired - Lifetime
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- 1999-06-14 SK SK1898-2000A patent/SK286640B6/sk not_active IP Right Cessation
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Also Published As

Publication number	Publication date
SK18982000A3 (sk)	2002-08-06
NO20006453D0 (no)	2000-12-18
HK1036801A1 (en)	2002-01-18
US6610847B2 (en)	2003-08-26
US6890929B2 (en)	2005-05-10
GEP20074227B (en)	2007-10-25
DE69916833D1 (de)	2004-06-03
CN1305480A (zh)	2001-07-25
AU3951899A (en)	2000-01-05
RS50087B (sr)	2009-01-22
DE69916833T2 (de)	2005-04-14
US20020019526A1 (en)	2002-02-14
NZ518444A (en)	2004-04-30
TW505646B (en)	2002-10-11
KR100415791B1 (ko)	2004-01-24
JP4971068B2 (ja)	2012-07-11
ID26698A (id)	2001-02-01
SK286640B6 (sk)	2009-03-05
CA2335492A1 (en)	1999-12-23
JP4666762B2 (ja)	2011-04-06
BG105129A (en)	2001-11-30
HRP20000885A2 (en)	2001-10-31
AP1021A (en)	2001-11-09
GT199900090A (es)	2000-12-09
NO2014012I1 (no)	2014-06-02
EA200001203A1 (ru)	2001-06-25
PL345123A1 (en)	2001-12-03
KR20010053004A (ko)	2001-06-25
NO318784B1 (no)	2005-05-09
US7687507B2 (en)	2010-03-30
TR200003719T2 (tr)	2001-03-21
IL139586A0 (en)	2002-02-10
FR14C0019I2 (fr)	2015-01-02
CA2335492C (en)	2005-05-17
JP2002518393A (ja)	2002-06-25
HUP0102574A2 (hu)	2001-11-28
PA8476001A1 (es)	2003-09-05
TNSN99126A1 (fr)	2005-11-10
EP1087970B1 (de)	2004-04-28
ES2219018T3 (es)	2004-11-16
PL198640B1 (pl)	2008-07-31
MY125916A (en)	2006-08-30
DK1087970T3 (da)	2004-08-02
PE20000698A1 (es)	2000-08-19
BG65119B1 (bg)	2007-03-30
EA005852B1 (ru)	2005-06-30
HRP20000885B1 (hr)	2007-03-31
AR016499A1 (es)	2001-07-04
ATE265458T1 (de)	2004-05-15
US20050171128A1 (en)	2005-08-04
MA26654A1 (fr)	2004-12-20
CN1128800C (zh)	2003-11-26
YU78500A (sh)	2003-04-30
US20030212273A1 (en)	2003-11-13
SA99200283B1 (ar)	2006-03-25
PT1087970E (pt)	2004-06-30
JP2012041365A (ja)	2012-03-01
AP9901584A0 (en)	1999-06-30
FR14C0019I1 (de)	2014-04-11
HUP0102574A3 (en)	2002-01-28
NO20006453L (no)	2001-02-05
CZ20004727A3 (cs)	2002-03-13
WO1999065908A1 (en)	1999-12-23
JP2007284455A (ja)	2007-11-01
EP1087970A1 (de)	2001-04-04
BR9911365A (pt)	2001-03-13

Publication	Publication Date	Title
OA11572A (en)	2004-07-01	PyrroloÄ2,3-düpyrimidine compounds.
EP1666481B1 (de)	2012-09-19	3-((3R,4R)-4-Methyl-3-[methyl-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-amino]-piperidinyl)-3-oxo-propionitrile als Proteinkinase Inhibitor
CA2335186C (en)	2005-03-29	Pyrrolo[2,3-d]pyrimidine compounds
MXPA05005403A (es)	2005-08-03	Derivados de 3-amino-piperadina y metodos de fabricacion.
HUE030714T2 (en)	2017-05-29	Cdk inhibitors
JP2008505100A (ja)	2008-02-21	ガンマ−セクレターゼ阻害剤としての置換ｎ−アリールスルホニル複素環アミン
AU2003234874B2 (en)	2004-09-02	Pyrrolo[2,3-d]pyrimidine Compounds
MXPA00012622A (en)	2001-07-31	PYRROLO[2,3-d]PYRIMIDINE COMPOUNDS
MXPA00012853A (en)	2001-09-07	PYRROLO[2,3-d]PYRIMIDINE COMPOUNDS