ZA200400574B - Thienopyrimidinediones and their use in the modulation of autoimmune disease. - Google Patents

Thienopyrimidinediones and their use in the modulation of autoimmune disease. Download PDF

Info

Publication number: ZA200400574B
Authority: ZA; South Africa
Prior art keywords: methyl; dione; pyrimidine; hydroxyisoxazolidin; ylcarbonyl
Prior art date: 2001-07-28

Application number

ZA200400574A

Other languages

English (en)

Inventor

Rachel Heulwen Reynolds

Rukhsana Tasneem Rasul

Martin Edward Cooper

Anthony Howard Ingall

Simon David Guile

Original Assignee

Astrazeneca Ab

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.)

2001-07-28

Filing date

2004-01-26

Publication date

2005-04-26

2004-01-26 Application filed by Astrazeneca Ab filed Critical Astrazeneca Ab

2005-04-26 Publication of ZA200400574B publication Critical patent/ZA200400574B/en

Links

208000023275 Autoimmune disease Diseases 0.000 title description 6
-1 isoxazolidin-2-ylcarbonyl Chemical group 0.000 claims description 182
150000001875 compounds Chemical class 0.000 claims description 59
229910052757 nitrogen Inorganic materials 0.000 claims description 30
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 27
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 26
150000003839 salts Chemical class 0.000 claims description 23
238000000034 method Methods 0.000 claims description 21
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
125000001424 substituent group Chemical group 0.000 claims description 19
125000003118 aryl group Chemical group 0.000 claims description 18
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
239000000203 mixture Substances 0.000 claims description 17
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 15
239000005864 Sulphur Chemical group 0.000 claims description 14
125000005842 heteroatom Chemical group 0.000 claims description 14
125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
125000004043 oxo group Chemical group O=* 0.000 claims description 13
229910052760 oxygen Inorganic materials 0.000 claims description 13
239000001301 oxygen Chemical group 0.000 claims description 13
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 11
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 10
125000000464 thioxo group Chemical group S=* 0.000 claims description 10
JGOOQALRLGHKIY-UHFFFAOYSA-N 1h-thieno[2,3-d]pyrimidine-2,4-dione Chemical compound O=C1NC(=O)NC2=C1C=CS2 JGOOQALRLGHKIY-UHFFFAOYSA-N 0.000 claims description 9
125000000623 heterocyclic group Chemical group 0.000 claims description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
229910052736 halogen Inorganic materials 0.000 claims description 8
150000002367 halogens Chemical class 0.000 claims description 8
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 7
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 7
125000004093 cyano group Chemical group *C#N 0.000 claims description 7
125000002883 imidazolyl group Chemical group 0.000 claims description 7
125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 7
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 7
229940002612 prodrug Drugs 0.000 claims description 7
239000000651 prodrug Substances 0.000 claims description 7
125000003226 pyrazolyl group Chemical group 0.000 claims description 7
125000004385 trihaloalkyl group Chemical group 0.000 claims description 7
210000001744 T-lymphocyte Anatomy 0.000 claims description 6
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 6
125000005493 quinolyl group Chemical group 0.000 claims description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
125000004122 cyclic group Chemical group 0.000 claims description 5
125000004982 dihaloalkyl group Chemical group 0.000 claims description 5
125000001188 haloalkyl group Chemical group 0.000 claims description 5
125000001041 indolyl group Chemical group 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
125000005843 halogen group Chemical group 0.000 claims description 4
125000000842 isoxazolyl group Chemical group 0.000 claims description 4
230000035755 proliferation Effects 0.000 claims description 4
125000004076 pyridyl group Chemical group 0.000 claims description 4
125000000168 pyrrolyl group Chemical group 0.000 claims description 4
125000006413 ring segment Chemical group 0.000 claims description 4
238000002560 therapeutic procedure Methods 0.000 claims description 4
KKZUMAMOMRDVKA-UHFFFAOYSA-N 2-chloropropane Chemical group [CH2]C(C)Cl KKZUMAMOMRDVKA-UHFFFAOYSA-N 0.000 claims description 3
125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
239000008194 pharmaceutical composition Substances 0.000 claims description 3
125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
230000015572 biosynthetic process Effects 0.000 claims description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
239000003814 drug Substances 0.000 claims description 2
238000003786 synthesis reaction Methods 0.000 claims description 2
239000000126 substance Substances 0.000 claims 14
ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 claims 12
206010062016 Immunosuppression Diseases 0.000 claims 3
208000027771 Obstructive airways disease Diseases 0.000 claims 3
201000010099 disease Diseases 0.000 claims 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
230000001506 immunosuppresive effect Effects 0.000 claims 3
230000002401 inhibitory effect Effects 0.000 claims 3
230000002441 reversible effect Effects 0.000 claims 3
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 2
NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims 1
CIISBYKBBMFLEZ-UHFFFAOYSA-N 1,2-oxazolidine Chemical compound C1CNOC1 CIISBYKBBMFLEZ-UHFFFAOYSA-N 0.000 claims 1
JWADHAVOUUUADB-AWEZNQCLSA-N 1-ethyl-5-[(4s)-4-hydroxy-1,2-oxazolidine-2-carbonyl]-3-methyl-6-[(2-propylbenzimidazol-1-yl)methyl]thieno[2,3-d]pyrimidine-2,4-dione Chemical compound CCCC1=NC2=CC=CC=C2N1CC=1SC=2N(CC)C(=O)N(C)C(=O)C=2C=1C(=O)N1C[C@H](O)CO1 JWADHAVOUUUADB-AWEZNQCLSA-N 0.000 claims 1
OAOKFYWAUWUPNT-UHFFFAOYSA-N 5-(4-hydroxy-1,2-oxazolidine-2-carbonyl)-3-methyl-1-(2-methylpropyl)-6-(quinolin-5-ylmethyl)thieno[2,3-d]pyrimidine-2,4-dione Chemical compound C1=2C(=O)N(C)C(=O)N(CC(C)C)C=2SC(CC=2C3=CC=CN=C3C=CC=2)=C1C(=O)N1CC(O)CO1 OAOKFYWAUWUPNT-UHFFFAOYSA-N 0.000 claims 1
FOUGTHXAKKBTGL-INIZCTEOSA-N 5-[(4s)-4-hydroxy-1,2-oxazolidine-2-carbonyl]-3-methyl-1-(2-methylpropyl)-6-(quinolin-4-ylmethyl)thieno[2,3-d]pyrimidine-2,4-dione Chemical compound C1=2C(=O)N(C)C(=O)N(CC(C)C)C=2SC(CC=2C3=CC=CC=C3N=CC=2)=C1C(=O)N1C[C@H](O)CO1 FOUGTHXAKKBTGL-INIZCTEOSA-N 0.000 claims 1
OKAJAHIFZHXGQD-AWEZNQCLSA-N 5-[(4s)-4-hydroxy-1,2-oxazolidine-2-carbonyl]-3-methyl-1-(2-methylpropyl)-6-(quinoline-4-carbonyl)thieno[2,3-d]pyrimidine-2,4-dione Chemical compound C1=2C(=O)N(C)C(=O)N(CC(C)C)C=2SC(C(=O)C=2C3=CC=CC=C3N=CC=2)=C1C(=O)N1C[C@H](O)CO1 OKAJAHIFZHXGQD-AWEZNQCLSA-N 0.000 claims 1
SYABSTPXYAKTOJ-AWEZNQCLSA-N 5-[(4s)-4-hydroxy-1,2-oxazolidine-2-carbonyl]-3-methyl-1-(2-methylpropyl)-6-[(1,3,5-trimethylpyrazol-4-yl)methyl]thieno[2,3-d]pyrimidine-2,4-dione Chemical compound C([C@@H](O)C1)ON1C(=O)C=1C=2C(=O)N(C)C(=O)N(CC(C)C)C=2SC=1CC=1C(C)=NN(C)C=1C SYABSTPXYAKTOJ-AWEZNQCLSA-N 0.000 claims 1
KWUIRMHYFXHDFM-LBPRGKRZSA-N 5-[(4s)-4-hydroxy-1,2-oxazolidine-2-carbonyl]-3-methyl-1-(2-methylpropyl)-6-[(2-methylsulfanylimidazol-1-yl)methyl]thieno[2,3-d]pyrimidine-2,4-dione Chemical compound CSC1=NC=CN1CC1=C(C(=O)N2OC[C@@H](O)C2)C(C(=O)N(C)C(=O)N2CC(C)C)=C2S1 KWUIRMHYFXHDFM-LBPRGKRZSA-N 0.000 claims 1
MONIFZUOJGZTAE-ZDUSSCGKSA-N 5-[(4s)-4-hydroxy-1,2-oxazolidine-2-carbonyl]-3-methyl-1-(2-methylpropyl)-6-[(2-oxo-3h-benzimidazol-1-yl)methyl]thieno[2,3-d]pyrimidine-2,4-dione Chemical compound C1=2C(=O)N(C)C(=O)N(CC(C)C)C=2SC(CN2C(NC3=CC=CC=C32)=O)=C1C(=O)N1C[C@H](O)CO1 MONIFZUOJGZTAE-ZDUSSCGKSA-N 0.000 claims 1
MXQQSPJNKRUPKR-HNNXBMFYSA-N 5-[(4s)-4-hydroxy-1,2-oxazolidine-2-carbonyl]-3-methyl-1-propan-2-yl-6-(quinolin-4-ylmethyl)thieno[2,3-d]pyrimidine-2,4-dione Chemical compound C1=2C(=O)N(C)C(=O)N(C(C)C)C=2SC(CC=2C3=CC=CC=C3N=CC=2)=C1C(=O)N1C[C@H](O)CO1 MXQQSPJNKRUPKR-HNNXBMFYSA-N 0.000 claims 1
HXZVKQYSAPGSDO-HNNXBMFYSA-N 5-[(4s)-4-hydroxy-1,2-oxazolidine-2-carbonyl]-3-methyl-1-propyl-6-(quinolin-4-ylmethyl)thieno[2,3-d]pyrimidine-2,4-dione Chemical compound C1=2C(=O)N(C)C(=O)N(CCC)C=2SC(CC=2C3=CC=CC=C3N=CC=2)=C1C(=O)N1C[C@H](O)CO1 HXZVKQYSAPGSDO-HNNXBMFYSA-N 0.000 claims 1
YVJYZPRWQVUGQK-LBPRGKRZSA-N 5-[(4s)-4-hydroxy-1,2-oxazolidine-2-carbonyl]-3-methyl-6-[(2-oxo-3h-benzimidazol-1-yl)methyl]-1-propan-2-ylthieno[2,3-d]pyrimidine-2,4-dione Chemical compound C1=2C(=O)N(C)C(=O)N(C(C)C)C=2SC(CN2C(NC3=CC=CC=C32)=O)=C1C(=O)N1C[C@H](O)CO1 YVJYZPRWQVUGQK-LBPRGKRZSA-N 0.000 claims 1
CYXVQFUBNAVJSY-KRWDZBQOSA-N 5-[(4s)-4-hydroxy-1,2-oxazolidine-2-carbonyl]-3-methyl-6-[(5-methyl-3-phenyl-1h-pyrazol-4-yl)methyl]-1-(2-methylpropyl)thieno[2,3-d]pyrimidine-2,4-dione Chemical compound C([C@@H](O)C1)ON1C(=O)C=1C=2C(=O)N(C)C(=O)N(CC(C)C)C=2SC=1CC1=C(C)NN=C1C1=CC=CC=C1 CYXVQFUBNAVJSY-KRWDZBQOSA-N 0.000 claims 1
GSGSGKQSENPYHG-VIFPVBQESA-N 6-[(2-bromo-4,5-dichloroimidazol-1-yl)methyl]-5-[(4s)-4-hydroxy-1,2-oxazolidine-2-carbonyl]-3-methyl-1-(2-methylpropyl)thieno[2,3-d]pyrimidine-2,4-dione Chemical compound C([C@@H](O)C1)ON1C(=O)C=1C=2C(=O)N(C)C(=O)N(CC(C)C)C=2SC=1CN1C(Br)=NC(Cl)=C1Cl GSGSGKQSENPYHG-VIFPVBQESA-N 0.000 claims 1
NWDXTHRUMCBLPT-IBGZPJMESA-N 6-[(3,5-dimethyl-1-phenylpyrazol-4-yl)methyl]-5-[(4s)-4-hydroxy-1,2-oxazolidine-2-carbonyl]-3-methyl-1-(2-methylpropyl)thieno[2,3-d]pyrimidine-2,4-dione Chemical compound C([C@@H](O)C1)ON1C(=O)C=1C=2C(=O)N(C)C(=O)N(CC(C)C)C=2SC=1CC(=C1C)C(C)=NN1C1=CC=CC=C1 NWDXTHRUMCBLPT-IBGZPJMESA-N 0.000 claims 1
UAXYKEAANLHJGN-SFHVURJKSA-N 6-[(3,5-dimethyl-1-phenylpyrazol-4-yl)methyl]-5-[(4s)-4-hydroxy-1,2-oxazolidine-2-carbonyl]-3-methyl-1-propylthieno[2,3-d]pyrimidine-2,4-dione Chemical compound C([C@@H](O)C1)ON1C(=O)C=1C=2C(=O)N(C)C(=O)N(CCC)C=2SC=1CC(=C1C)C(C)=NN1C1=CC=CC=C1 UAXYKEAANLHJGN-SFHVURJKSA-N 0.000 claims 1
VCFBFOISICPBER-INIZCTEOSA-N 6-[(3,5-dimethyl-1-propan-2-ylpyrazol-4-yl)methyl]-5-[(4s)-4-hydroxy-1,2-oxazolidine-2-carbonyl]-3-methyl-1-(2-methylpropyl)thieno[2,3-d]pyrimidine-2,4-dione Chemical compound C([C@@H](O)C1)ON1C(=O)C=1C=2C(=O)N(C)C(=O)N(CC(C)C)C=2SC=1CC=1C(C)=NN(C(C)C)C=1C VCFBFOISICPBER-INIZCTEOSA-N 0.000 claims 1
FXYDHGALICIHIR-ZDUSSCGKSA-N 6-[(3,5-dimethyl-1h-pyrazol-4-yl)methyl]-3-ethyl-5-[(4s)-4-hydroxy-1,2-oxazolidine-2-carbonyl]-1-propan-2-ylthieno[2,3-d]pyrimidine-2,4-dione Chemical compound C([C@@H](O)C1)ON1C(=O)C=1C=2C(=O)N(CC)C(=O)N(C(C)C)C=2SC=1CC=1C(C)=NNC=1C FXYDHGALICIHIR-ZDUSSCGKSA-N 0.000 claims 1
QKBZODOPLHOHSA-LBPRGKRZSA-N 6-[(3,5-dimethyl-1h-pyrazol-4-yl)methyl]-5-[(4s)-4-hydroxy-1,2-oxazolidine-2-carbonyl]-3-methyl-1-propylthieno[2,3-d]pyrimidine-2,4-dione Chemical compound C([C@@H](O)C1)ON1C(=O)C=1C=2C(=O)N(C)C(=O)N(CCC)C=2SC=1CC=1C(C)=NNC=1C QKBZODOPLHOHSA-LBPRGKRZSA-N 0.000 claims 1
IBKJEDNPWVCURQ-NSHDSACASA-N 6-[(4,5-dichloro-2-methylimidazol-1-yl)methyl]-5-[(4s)-4-hydroxy-1,2-oxazolidine-2-carbonyl]-3-methyl-1-(2-methylpropyl)thieno[2,3-d]pyrimidine-2,4-dione Chemical compound C([C@@H](O)C1)ON1C(=O)C=1C=2C(=O)N(C)C(=O)N(CC(C)C)C=2SC=1CN1C(C)=NC(Cl)=C1Cl IBKJEDNPWVCURQ-NSHDSACASA-N 0.000 claims 1
VGGIJLVSICXJBM-HNNXBMFYSA-N 6-[(8-fluoroquinolin-4-yl)methyl]-5-[(4s)-4-hydroxy-1,2-oxazolidine-2-carbonyl]-3-methyl-1-(2-methylpropyl)thieno[2,3-d]pyrimidine-2,4-dione Chemical compound C1=2C(=O)N(C)C(=O)N(CC(C)C)C=2SC(CC=2C3=CC=CC(F)=C3N=CC=2)=C1C(=O)N1C[C@H](O)CO1 VGGIJLVSICXJBM-HNNXBMFYSA-N 0.000 claims 1
UVWGPIMVDAKHKN-AWEZNQCLSA-N 6-[[2-(hydroxymethyl)benzimidazol-1-yl]methyl]-5-[(4s)-4-hydroxy-1,2-oxazolidine-2-carbonyl]-3-methyl-1-(2-methylpropyl)thieno[2,3-d]pyrimidine-2,4-dione Chemical compound C1=2C(=O)N(C)C(=O)N(CC(C)C)C=2SC(CN2C3=CC=CC=C3N=C2CO)=C1C(=O)N1C[C@H](O)CO1 UVWGPIMVDAKHKN-AWEZNQCLSA-N 0.000 claims 1
TVOYGIMHJBLGHY-ZDUSSCGKSA-N 6-[[2-(hydroxymethyl)benzimidazol-1-yl]methyl]-5-[(4s)-4-hydroxy-1,2-oxazolidine-2-carbonyl]-3-methyl-1-propylthieno[2,3-d]pyrimidine-2,4-dione Chemical compound C1=2C(=O)N(C)C(=O)N(CCC)C=2SC(CN2C3=CC=CC=C3N=C2CO)=C1C(=O)N1C[C@H](O)CO1 TVOYGIMHJBLGHY-ZDUSSCGKSA-N 0.000 claims 1
JJYWRSPCUYGYHF-JTQLQIEISA-N 6-[[4,5-dichloro-2-(hydroxymethyl)imidazol-1-yl]methyl]-5-[(4s)-4-hydroxy-1,2-oxazolidine-2-carbonyl]-3-methyl-1-(2-methylpropyl)thieno[2,3-d]pyrimidine-2,4-dione Chemical compound C([C@@H](O)C1)ON1C(=O)C=1C=2C(=O)N(C)C(=O)N(CC(C)C)C=2SC=1CN1C(CO)=NC(Cl)=C1Cl JJYWRSPCUYGYHF-JTQLQIEISA-N 0.000 claims 1
239000002671 adjuvant Substances 0.000 claims 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
239000003085 diluting agent Substances 0.000 claims 1
125000000524 functional group Chemical group 0.000 claims 1
239000012453 solvate Substances 0.000 claims 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 9
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 5
150000002148 esters Chemical class 0.000 description 5
125000000714 pyrimidinyl group Chemical group 0.000 description 5
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
125000001544 thienyl group Chemical group 0.000 description 4
239000002253 acid Substances 0.000 description 3
125000002619 bicyclic group Chemical group 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
125000005946 imidazo[1,2-a]pyridyl group Chemical group 0.000 description 3
238000001727 in vivo Methods 0.000 description 3
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 3
RBNBDIMXFJYDLQ-UHFFFAOYSA-N thieno[3,2-d]pyrimidine Chemical group C1=NC=C2SC=CC2=N1 RBNBDIMXFJYDLQ-UHFFFAOYSA-N 0.000 description 3
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
WYLSGWZVDHQRNX-UHFFFAOYSA-N 2-(3,4-dimethoxy-n-(4-methylphenyl)sulfonylanilino)-n-(2,4-dimethylpentan-3-yl)acetamide Chemical compound C1=C(OC)C(OC)=CC=C1N(CC(=O)NC(C(C)C)C(C)C)S(=O)(=O)C1=CC=C(C)C=C1 WYLSGWZVDHQRNX-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
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 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
229910019142 PO4 Inorganic materials 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
125000003342 alkenyl group Chemical group 0.000 description 2
125000000304 alkynyl group Chemical group 0.000 description 2
230000009286 beneficial effect Effects 0.000 description 2
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Substances OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 2
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
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239000001257 hydrogen Substances 0.000 description 2
230000028993 immune response Effects 0.000 description 2
150000007529 inorganic bases Chemical class 0.000 description 2
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
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150000007530 organic bases Chemical class 0.000 description 2
235000021317 phosphate Nutrition 0.000 description 2
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
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125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 1
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GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
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125000005117 dialkylcarbamoyl group Chemical group 0.000 description 1
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229940079593 drug Drugs 0.000 description 1
238000009510 drug design Methods 0.000 description 1
238000009509 drug development Methods 0.000 description 1
238000011067 equilibration Methods 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
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229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
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VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
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230000004054 inflammatory process Effects 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
150000002485 inorganic esters Chemical class 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
150000003893 lactate salts Chemical class 0.000 description 1
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125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
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150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
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206010039073 rheumatoid arthritis Diseases 0.000 description 1
239000007787 solid Substances 0.000 description 1
150000003890 succinate salts Chemical class 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
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1

Classifications

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- A61P21/04—Drugs for disorders of the muscular or neuromuscular system for myasthenia gravis
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ZA200400574A 2001-07-28 2004-01-26 Thienopyrimidinediones and their use in the modulation of autoimmune disease. ZA200400574B (en)

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GBGB0118479.5A GB0118479D0 (en)	2001-07-28	2001-07-28	Novel compounds

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US (2)	US7384950B2 (de)
EP (1)	EP1414825B9 (de)
JP (1)	JP4456364B2 (de)
KR (1)	KR100897469B1 (de)
CN (1)	CN1324033C (de)
AR (1)	AR038000A1 (de)
AT (1)	ATE374204T1 (de)
AU (1)	AU2002319469B2 (de)
BR (1)	BR0211262A (de)
CA (1)	CA2453274A1 (de)
DE (1)	DE60222671T2 (de)
ES (1)	ES2292784T3 (de)
GB (1)	GB0118479D0 (de)
HU (1)	HUP0402336A3 (de)
IL (2)	IL159785A0 (de)
IS (1)	IS2598B (de)
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NO (1)	NO328713B1 (de)
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PL (1)	PL211351B1 (de)
RU (1)	RU2294937C9 (de)
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SE9801399D0 (sv)	1998-04-21	1998-04-21	Astra Pharma Prod	Method and apparatus for filling containers
GB0117583D0 (en) *	2001-07-19	2001-09-12	Astrazeneca Ab	Novel compounds
GB0118479D0 (en) *	2001-07-28	2001-09-19	Astrazeneca Ab	Novel compounds
CA2462200A1 (en)	2001-08-10	2003-02-20	Palatin Technologies, Inc.	Peptidomimetics of biologically active metallopeptides
US7732451B2 (en)	2001-08-10	2010-06-08	Palatin Technologies, Inc.	Naphthalene-containing melanocortin receptor-specific small molecule
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2001
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Also Published As

Publication number	Publication date
AR038000A1 (es)	2004-12-22
ATE374204T1 (de)	2007-10-15
IL159785A (en)	2009-11-18
NZ530495A (en)	2005-07-29
JP4456364B2 (ja)	2010-04-28
HK1065785A1 (en)	2005-03-04
DE60222671T2 (de)	2008-06-26
EP1414825B1 (de)	2007-09-26
CN1538970A (zh)	2004-10-20
CN1324033C (zh)	2007-07-04
EP1414825B9 (de)	2009-09-16
IS2598B (is)	2010-03-15
KR20040017355A (ko)	2004-02-26
NO328713B1 (no)	2010-05-03
PL369232A1 (en)	2005-04-18
US7384950B2 (en)	2008-06-10
HUP0402336A2 (hu)	2005-02-28
RU2294937C2 (ru)	2007-03-10
EP1414825A1 (de)	2004-05-06
US20080207642A1 (en)	2008-08-28
US20040254198A1 (en)	2004-12-16
MXPA04000677A (es)	2004-04-05
NO20040364L (no)	2004-03-29
RU2294937C9 (ru)	2007-07-20
CA2453274A1 (en)	2003-02-13
AU2002319469B8 (en)	2003-02-17
JP2004538316A (ja)	2004-12-24
RU2004102392A (ru)	2005-07-10
KR100897469B1 (ko)	2009-05-14
IS7118A (is)	2004-01-19
HUP0402336A3 (en)	2008-09-29
ES2292784T3 (es)	2008-03-16
MY138145A (en)	2009-04-30
BR0211262A (pt)	2004-07-20
PL211351B1 (pl)	2012-05-31
WO2003011868A1 (en)	2003-02-13
DE60222671D1 (de)	2007-11-08
AU2002319469B2 (en)	2007-08-09
IL159785A0 (en)	2004-06-20
GB0118479D0 (en)	2001-09-19

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