UA72290C2 - СПОЛУКИ ПІРОЛО[2.3-d]ПІРИМІДИНУ, ФАРМАЦЕВТИЧНА КОМПОЗИЦІЯ (ВАРІАНТИ), СПОСІБ ІНГІБУВАННЯ ПРОТЕЇНКІНАЗ АБО JANUS КІНАЗИ 3 (ВАРІАНТИ) - Google Patents

СПОЛУКИ ПІРОЛО[2.3-d]ПІРИМІДИНУ, ФАРМАЦЕВТИЧНА КОМПОЗИЦІЯ (ВАРІАНТИ), СПОСІБ ІНГІБУВАННЯ ПРОТЕЇНКІНАЗ АБО JANUS КІНАЗИ 3 (ВАРІАНТИ) Download PDF

Info

Publication number: UA72290C2
Authority: UA; Ukraine
Prior art keywords: formula; methyl; compounds; pyrrolo; alkyl
Prior art date: 1999-12-10

Application number

UA2002064708A

Other languages

English (en)

Russian (ru)

Ukrainian (uk)

Inventor

Тодд Ендрю Блуменкопф

Марк Едвард Фленеген

Майкл Джон Манчхоф

Original Assignee

Пфайзер Продактс Інк.

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

2005-02-15

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=22618882&utm_source=***_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=UA72290(C2) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

2000-11-23 Application filed by Пфайзер Продактс Інк. filed Critical Пфайзер Продактс Інк.

2005-02-15 Publication of UA72290C2 publication Critical patent/UA72290C2/uk

Links

150000001875 compounds Chemical class 0.000 title abstract description 112
102000001253 Protein Kinase Human genes 0.000 title abstract description 5
108060006633 protein kinase Proteins 0.000 title abstract description 5
102000006500 Janus Kinase 3 Human genes 0.000 title abstract 2
108010019421 Janus Kinase 3 Proteins 0.000 title abstract 2
238000000034 method Methods 0.000 title description 23
239000008194 pharmaceutical composition Substances 0.000 title description 5
230000005764 inhibitory process Effects 0.000 title description 4
JJTNLWSCFYERCK-UHFFFAOYSA-N 7h-pyrrolo[2,3-d]pyrimidine Chemical compound N1=CN=C2NC=CC2=C1 JJTNLWSCFYERCK-UHFFFAOYSA-N 0.000 title 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 6
208000006673 asthma Diseases 0.000 abstract description 4
206010012601 diabetes mellitus Diseases 0.000 abstract description 4
206010039073 rheumatoid arthritis Diseases 0.000 abstract description 4
208000023275 Autoimmune disease Diseases 0.000 abstract description 3
206010009900 Colitis ulcerative Diseases 0.000 abstract description 3
206010012438 Dermatitis atopic Diseases 0.000 abstract description 3
206010028980 Neoplasm Diseases 0.000 abstract description 3
201000004681 Psoriasis Diseases 0.000 abstract description 3
208000024799 Thyroid disease Diseases 0.000 abstract description 3
201000006704 Ulcerative Colitis Diseases 0.000 abstract description 3
201000008937 atopic dermatitis Diseases 0.000 abstract description 3
230000001363 autoimmune Effects 0.000 abstract description 3
201000011510 cancer Diseases 0.000 abstract description 3
208000032839 leukemia Diseases 0.000 abstract description 3
206010025135 lupus erythematosus Diseases 0.000 abstract description 3
201000006417 multiple sclerosis Diseases 0.000 abstract description 3
210000000056 organ Anatomy 0.000 abstract description 3
208000024827 Alzheimer disease Diseases 0.000 abstract description 2
206010067584 Type 1 diabetes mellitus Diseases 0.000 abstract description 2
239000003112 inhibitor Substances 0.000 abstract description 2
201000010099 disease Diseases 0.000 abstract 1
229940125721 immunosuppressive agent Drugs 0.000 abstract 1
239000003018 immunosuppressive agent Substances 0.000 abstract 1
238000002560 therapeutic procedure Methods 0.000 abstract 1
238000002054 transplantation Methods 0.000 abstract 1
229910052724 xenon Inorganic materials 0.000 abstract 1
FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 abstract 1
-1 nitro, carboxy Chemical group 0.000 description 56
125000000217 alkyl group Chemical group 0.000 description 37
238000006243 chemical reaction Methods 0.000 description 28
125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 28
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 25
150000003839 salts Chemical class 0.000 description 25
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
239000000203 mixture Substances 0.000 description 20
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
150000001412 amines Chemical class 0.000 description 15
239000000243 solution Substances 0.000 description 14
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
239000002253 acid Substances 0.000 description 11
239000002904 solvent Substances 0.000 description 11
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
239000002585 base Substances 0.000 description 10
125000000592 heterocycloalkyl group Chemical group 0.000 description 10
239000011541 reaction mixture Substances 0.000 description 10
125000003545 alkoxy group Chemical group 0.000 description 9
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 9
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
210000004027 cell Anatomy 0.000 description 8
235000019441 ethanol Nutrition 0.000 description 8
125000006239 protecting 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
241000124008 Mammalia Species 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
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
239000003795 chemical substances by application Substances 0.000 description 7
229910052739 hydrogen Inorganic materials 0.000 description 7
239000001257 hydrogen Substances 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
229910014585 C2-Ce Inorganic materials 0.000 description 6
108091000080 Phosphotransferase Proteins 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
210000001744 T-lymphocyte Anatomy 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
125000003118 aryl group Chemical group 0.000 description 6
230000003197 catalytic effect Effects 0.000 description 6
230000001419 dependent effect Effects 0.000 description 6
229910052757 nitrogen Inorganic materials 0.000 description 6
102000020233 phosphotransferase Human genes 0.000 description 6
230000035755 proliferation Effects 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
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 5
239000000443 aerosol Substances 0.000 description 5
150000001447 alkali salts Chemical class 0.000 description 5
125000003282 alkyl amino group Chemical group 0.000 description 5
239000003153 chemical reaction reagent Substances 0.000 description 5
208000035475 disorder Diseases 0.000 description 5
125000004404 heteroalkyl group Chemical group 0.000 description 5
125000001072 heteroaryl group Chemical group 0.000 description 5
231100000252 nontoxic Toxicity 0.000 description 5
230000003000 nontoxic effect Effects 0.000 description 5
229910052763 palladium Inorganic materials 0.000 description 5
239000000651 prodrug Substances 0.000 description 5
229940002612 prodrug Drugs 0.000 description 5
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 4
229930105110 Cyclosporin A Natural products 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-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
125000004656 alkyl sulfonylamino 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
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
229910052794 bromium Inorganic materials 0.000 description 4
150000001768 cations Chemical class 0.000 description 4
229960001265 ciclosporin Drugs 0.000 description 4
RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical group C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 description 4
238000009472 formulation Methods 0.000 description 4
125000005843 halogen group Chemical group 0.000 description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
239000002609 medium Substances 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
239000000047 product Substances 0.000 description 4
QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 4
229940080818 propionamide Drugs 0.000 description 4
239000000377 silicon dioxide Substances 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
239000011734 sodium Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
229960001967 tacrolimus Drugs 0.000 description 4
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 4
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
SOEKBHFSOCQNFZ-UHFFFAOYSA-N 4-methyl-3-(methylamino)piperidine-1-carboxylic acid Chemical compound CNC1CN(C(O)=O)CCC1C SOEKBHFSOCQNFZ-UHFFFAOYSA-N 0.000 description 3
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
241000282412 Homo Species 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
230000001476 alcoholic effect Effects 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
125000000304 alkynyl group Chemical group 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
125000000539 amino acid group Chemical group 0.000 description 3
229940077388 benzenesulfonate Drugs 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
230000015572 biosynthetic process Effects 0.000 description 3
239000002775 capsule Substances 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
239000012039 electrophile Substances 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
239000012458 free base Substances 0.000 description 3
230000002401 inhibitory effect Effects 0.000 description 3
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 3
150000004702 methyl esters Chemical class 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
150000007522 mineralic acids Chemical class 0.000 description 3
MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 3
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
150000007524 organic acids Chemical class 0.000 description 3
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 3
239000000843 powder Substances 0.000 description 3
239000007921 spray Substances 0.000 description 3
239000003826 tablet Substances 0.000 description 3
238000012360 testing method Methods 0.000 description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 2
125000004209 (C1-C8) alkyl group Chemical group 0.000 description 2
125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 description 2
DNUTZBZXLPWRJG-UHFFFAOYSA-N 1-Piperidine carboxylic acid Chemical compound OC(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 2
208000011231 Crohn disease Diseases 0.000 description 2
YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 2
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
102000004190 Enzymes Human genes 0.000 description 2
108090000790 Enzymes Proteins 0.000 description 2
HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 description 2
229910019142 PO4 Inorganic materials 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
229960001138 acetylsalicylic acid Drugs 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
239000000654 additive Substances 0.000 description 2
150000001299 aldehydes Chemical class 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
125000003342 alkenyl group Chemical group 0.000 description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
125000004466 alkoxycarbonylamino group Chemical group 0.000 description 2
150000001350 alkyl halides Chemical class 0.000 description 2
125000004390 alkyl sulfonyl group Chemical group 0.000 description 2
125000004414 alkyl thio group Chemical group 0.000 description 2
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239000002260 anti-inflammatory agent Substances 0.000 description 2
230000003110 anti-inflammatory effect Effects 0.000 description 2
150000001503 aryl iodides Chemical class 0.000 description 2
229940092117 atgam Drugs 0.000 description 2
238000000065 atmospheric pressure chemical ionisation Methods 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
229960002170 azathioprine Drugs 0.000 description 2
UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 description 2
210000004369 blood Anatomy 0.000 description 2
239000008280 blood Substances 0.000 description 2
230000037396 body weight Effects 0.000 description 2
238000009835 boiling Methods 0.000 description 2
125000001246 bromo group Chemical group Br* 0.000 description 2
239000011575 calcium Substances 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
150000004657 carbamic acid derivatives Chemical class 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
239000000969 carrier Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
239000012230 colorless oil Substances 0.000 description 2
125000004093 cyano group Chemical group *C#N 0.000 description 2
125000004122 cyclic group Chemical group 0.000 description 2
125000000753 cycloalkyl group Chemical group 0.000 description 2
229960002806 daclizumab Drugs 0.000 description 2
229910052805 deuterium Inorganic materials 0.000 description 2
UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 description 2
229960003957 dexamethasone Drugs 0.000 description 2
UZBQIPPOMKBLAS-UHFFFAOYSA-N diethylazanide Chemical compound CC[N-]CC UZBQIPPOMKBLAS-UHFFFAOYSA-N 0.000 description 2
229910001882 dioxygen Inorganic materials 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
239000003937 drug carrier Substances 0.000 description 2
238000003818 flash chromatography Methods 0.000 description 2
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230000008054 signal transmission Effects 0.000 description 1
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235000017557 sodium bicarbonate Nutrition 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
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BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
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229910000104 sodium hydride Inorganic materials 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
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239000004334 sorbic acid Substances 0.000 description 1
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239000001119 stannous chloride Substances 0.000 description 1
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239000011550 stock solution Substances 0.000 description 1
229960005322 streptomycin Drugs 0.000 description 1
125000003011 styrenyl group Chemical class [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
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KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
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150000003456 sulfonamides Chemical class 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000002511 suppository base Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
125000004568 thiomorpholinyl group Chemical group 0.000 description 1
KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
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
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
229940029284 trichlorofluoromethane Drugs 0.000 description 1
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
LSGOVYNHVSXFFJ-UHFFFAOYSA-N vanadate(3-) Chemical compound [O-][V]([O-])([O-])=O LSGOVYNHVSXFFJ-UHFFFAOYSA-N 0.000 description 1
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Classifications

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- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

UA2002064708A 1999-12-10 2000-11-23 СПОЛУКИ ПІРОЛО[2.3-d]ПІРИМІДИНУ, ФАРМАЦЕВТИЧНА КОМПОЗИЦІЯ (ВАРІАНТИ), СПОСІБ ІНГІБУВАННЯ ПРОТЕЇНКІНАЗ АБО JANUS КІНАЗИ 3 (ВАРІАНТИ) UA72290C2 (uk)

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Cited By (4)

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US7923467B2 (en)	2003-05-30	2011-04-12	Ranbaxy Laboratories, Inc.	Substituted pyrrole derivatives and their use as HMG-CO inhibitors
US7671216B2 (en)	2005-11-08	2010-03-02	Ranbaxy Laboratories Limited	Process for preparation of (3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-[(4-hydroxy methyl phenyl amino) carbonyl]-pyrrol-1-yl]-3,5-dihydroxy-heptanoic acid hemi calcium salt
US7956198B2 (en)	2005-11-08	2011-06-07	Ranbaxy Laboratories, Limited	Pharmaceutical compositions
US8026377B2 (en)	2005-11-08	2011-09-27	Ranbaxy Laboratories, Limited	Process for (3R, 5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-[(4-hydroxy methyl phenyl amino) carbonyl]-pyrrol-1-yl]-3,5-dihydroxy-heptanoic acid hemi calcium salt

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ATE257157T1 (de)	2004-01-15
AR026534A1 (es)	2003-02-12
CN1195755C (zh)	2005-04-06
PA8507301A1 (es)	2002-02-21
DK1382339T3 (da)	2008-01-28
NZ518884A (en)	2004-02-27
NZ528905A (en)	2005-03-24
CN1409712A (zh)	2003-04-09
CY1108850T1 (el)	2014-07-02
ES2295495T3 (es)	2008-04-16
BR0016263A (pt)	2002-08-13
GT200000208A (es)	2002-06-01
OA12118A (en)	2006-05-04
US20040053947A1 (en)	2004-03-18
EA006227B1 (ru)	2005-10-27
EE05351B1 (et)	2010-10-15
TR200400105T4 (tr)	2004-02-23
SK7562002A3 (en)	2003-08-05
EA200200506A1 (ru)	2002-12-26
DE60007552T2 (de)	2004-09-23
WO2001042246A2 (en)	2001-06-14
US20050288313A1 (en)	2005-12-29
ES2208433T3 (es)	2004-06-16
HK1051195A1 (en)	2003-07-25
AP2002002543A0 (en)	2002-06-30
PT1235830E (pt)	2004-04-30
EP1235830B1 (en)	2004-01-02
EP1382339A1 (en)	2004-01-21
US20070292430A1 (en)	2007-12-20
PE20011096A1 (es)	2001-10-25
TR200201498T2 (tr)	2003-01-21
US20060241131A1 (en)	2006-10-26
JP4078074B2 (ja)	2008-04-23
US7842699B2 (en)	2010-11-30
IL149616A (en)	2010-02-17
MXPA02005675A (es)	2002-09-02
PL218519B1 (pl)	2014-12-31
KR20020061637A (ko)	2002-07-24
DK1235830T3 (da)	2004-03-29
HUP0203503A2 (hu)	2003-02-28
AU1295001A (en)	2001-06-18
BRPI0016263B1 (pt)	2016-07-26
TNSN00239A1 (fr)	2005-11-10
US6956041B2 (en)	2005-10-18
EG24399A (en)	2009-04-29
DZ3248A1 (fr)	2001-06-14
AP1905A (en)	2008-10-20
NO323378B1 (no)	2007-04-16
EP1235830A2 (en)	2002-09-04
TW200427453A (en)	2004-12-16
US7265221B2 (en)	2007-09-04
BG106855A (bg)	2002-12-29
US20010053782A1 (en)	2001-12-20
TWI248935B (en)	2006-02-11
MY130760A (en)	2007-07-31
KR100477818B1 (ko)	2005-03-22
HUP0203503A3 (en)	2004-12-28
HU229671B1 (en)	2014-04-28
HRP20020509A2 (en)	2004-08-31
IS2173B (is)	2006-11-15
US7601727B2 (en)	2009-10-13
US7091208B2 (en)	2006-08-15
GEP20053479B (en)	2005-03-25
PT1382339E (pt)	2008-02-06
PL355907A1 (en)	2004-05-31
YU41302A (sh)	2005-03-15
TWI264305B (en)	2006-10-21
ECSP003819A (es)	2001-06-11
RS51574B (sr)	2011-08-31
IS6383A (is)	2002-05-14
CZ20021846A3 (cs)	2003-06-18
CU23220A3 (es)	2007-07-20
DE60007552D1 (de)	2004-02-05
BRPI0016263B8 (pt)	2021-05-25
HRP20020509B1 (en)	2005-06-30
USRE41783E1 (en)	2010-09-28
JP2003516405A (ja)	2003-05-13
ATE380031T1 (de)	2007-12-15
DE60037345T2 (de)	2008-11-13
SK287188B6 (sk)	2010-02-08
CO5271665A1 (es)	2003-04-30
SV2002000236A (es)	2002-06-07
US20100035903A1 (en)	2010-02-11
ZA200204535B (en)	2003-09-29
CA2393640A1 (en)	2001-06-14
NO20022738D0 (no)	2002-06-07
EE200200304A (et)	2003-06-16
CA2393640C (en)	2006-09-05
HN2000000265A (es)	2001-04-11
NO20022738L (no)	2002-06-07
MA26851A1 (fr)	2004-12-20
UY26477A1 (es)	2001-06-29
BG65821B1 (bg)	2010-01-29
SI1235830T1 (en)	2004-06-30
DE60037345D1 (de)	2008-01-17
CR6655A (es)	2003-11-07
AU777911B2 (en)	2004-11-04
US6627754B2 (en)	2003-09-30
CZ303875B6 (cs)	2013-06-05
IL149616A0 (en)	2002-11-10
WO2001042246A3 (en)	2001-11-22
EP1382339B1 (en)	2007-12-05

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AU2004305317A1 (en)	2005-07-07	Pyrrolo [2,3-D] pyrimidine compounds for treating transplant rejection