CA2865167C - Heterocyclyl compounds - Google Patents

Heterocyclyl compounds Download PDF

Info

Publication number: CA2865167C
Authority: CA; Canada
Prior art keywords: alkyl; group; substituted; cycloalkyl; compound
Prior art date: 2012-03-14
Legal status (The legal status 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 status listed.): Expired - Fee Related

Application number

CA2865167A

Other languages

English (en)

French (fr)

Other versions

CA2865167A1 (en

Inventor

Bhavesh Dave

Rakesh Kumar Banerjee

Samiron Phukan

Abhijit Datta Khoje

Rajkumar HANGARGE

Jitendra Sambhaji Jadhav

Venkata P. Palle

Rajender Kumar Kamboj

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Lupin Ltd

Original Assignee

Lupin Ltd

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.)

2012-03-14

Filing date

2013-03-11

Publication date

2019-08-06

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=47997632&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=CA2865167(C) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

2013-03-11 Application filed by Lupin Ltd filed Critical Lupin Ltd

2013-09-19 Publication of CA2865167A1 publication Critical patent/CA2865167A1/en

2019-08-06 Application granted granted Critical

2019-08-06 Publication of CA2865167C publication Critical patent/CA2865167C/en

Status Expired - Fee Related legal-status Critical Current

2033-03-11 Anticipated expiration legal-status Critical

Links

125000000623 heterocyclic group Chemical group 0.000 title claims description 96
150000001875 compounds Chemical class 0.000 claims abstract description 166
125000001072 heteroaryl group Chemical group 0.000 claims abstract description 66
150000003839 salts Chemical class 0.000 claims abstract description 35
239000003814 drug Substances 0.000 claims abstract description 13
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 11
125000000217 alkyl group Chemical group 0.000 claims description 193
-1 perhaloalkyl Chemical group 0.000 claims description 117
125000000753 cycloalkyl group Chemical group 0.000 claims description 74
125000003342 alkenyl group Chemical group 0.000 claims description 67
125000003118 aryl group Chemical group 0.000 claims description 67
239000001257 hydrogen Substances 0.000 claims description 62
229910052739 hydrogen Inorganic materials 0.000 claims description 62
125000000392 cycloalkenyl group Chemical group 0.000 claims description 57
206010028980 Neoplasm Diseases 0.000 claims description 53
150000002431 hydrogen Chemical group 0.000 claims description 51
125000001424 substituent group Chemical group 0.000 claims description 50
229910052736 halogen Inorganic materials 0.000 claims description 48
150000002367 halogens Chemical group 0.000 claims description 48
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 35
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 30
208000035475 disorder Diseases 0.000 claims description 26
102000004232 Mitogen-Activated Protein Kinase Kinases Human genes 0.000 claims description 20
108090000744 Mitogen-Activated Protein Kinase Kinases Proteins 0.000 claims description 20
201000011510 cancer Diseases 0.000 claims description 20
125000004043 oxo group Chemical group O=* 0.000 claims description 20
238000011282 treatment Methods 0.000 claims description 20
125000004093 cyano group Chemical group *C#N 0.000 claims description 17
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
229910052799 carbon Inorganic materials 0.000 claims description 12
102000001291 MAP Kinase Kinase Kinase Human genes 0.000 claims description 11
108060006687 MAP kinase kinase kinase Proteins 0.000 claims description 11
125000001188 haloalkyl group Chemical group 0.000 claims description 11
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 10
230000002401 inhibitory effect Effects 0.000 claims description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
201000010099 disease Diseases 0.000 claims description 9
229910052757 nitrogen Inorganic materials 0.000 claims description 9
239000000546 pharmaceutical excipient Substances 0.000 claims description 9
230000035755 proliferation Effects 0.000 claims description 9
229910006074 SO2NH2 Inorganic materials 0.000 claims description 8
230000001404 mediated effect Effects 0.000 claims description 8
230000002062 proliferating effect Effects 0.000 claims description 8
206010039073 rheumatoid arthritis Diseases 0.000 claims description 8
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
241000124008 Mammalia Species 0.000 claims description 7
239000003937 drug carrier Substances 0.000 claims description 7
208000027866 inflammatory disease Diseases 0.000 claims description 7
229910052705 radium Inorganic materials 0.000 claims description 7
239000003085 diluting agent Substances 0.000 claims description 6
230000012010 growth Effects 0.000 claims description 6
208000037803 restenosis Diseases 0.000 claims description 6
229910052701 rubidium Inorganic materials 0.000 claims description 6
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
201000004681 Psoriasis Diseases 0.000 claims description 5
229910052740 iodine Inorganic materials 0.000 claims description 5
208000032839 leukemia Diseases 0.000 claims description 5
208000023275 Autoimmune disease Diseases 0.000 claims description 4
201000009030 Carcinoma Diseases 0.000 claims description 4
208000006011 Stroke Diseases 0.000 claims description 4
230000003463 hyperproliferative effect Effects 0.000 claims description 4
238000011321 prophylaxis Methods 0.000 claims description 4
SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 claims description 3
102000004190 Enzymes Human genes 0.000 claims description 3
108090000790 Enzymes Proteins 0.000 claims description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
238000011374 additional therapy Methods 0.000 claims description 3
229940125904 compound 1 Drugs 0.000 claims description 3
229940126543 compound 14 Drugs 0.000 claims description 3
229940125782 compound 2 Drugs 0.000 claims description 3
229940125810 compound 20 Drugs 0.000 claims description 3
230000000593 degrading effect Effects 0.000 claims description 3
229910052731 fluorine Inorganic materials 0.000 claims description 3
230000002147 killing effect Effects 0.000 claims description 3
AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 claims description 2
GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 claims description 2
GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 claims description 2
QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 claims description 2
IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 claims description 2
ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 claims description 2
UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 claims description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
208000020446 Cardiac disease Diseases 0.000 claims description 2
229940126657 Compound 17 Drugs 0.000 claims description 2
OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 claims description 2
208000012902 Nervous system disease Diseases 0.000 claims description 2
208000025966 Neurological disease Diseases 0.000 claims description 2
LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 claims description 2
201000004983 autoimmune atherosclerosis Diseases 0.000 claims description 2
238000002512 chemotherapy Methods 0.000 claims description 2
229940125773 compound 10 Drugs 0.000 claims description 2
229940125797 compound 12 Drugs 0.000 claims description 2
229940125758 compound 15 Drugs 0.000 claims description 2
229940126142 compound 16 Drugs 0.000 claims description 2
229940126086 compound 21 Drugs 0.000 claims description 2
229940126214 compound 3 Drugs 0.000 claims description 2
229940125898 compound 5 Drugs 0.000 claims description 2
230000001842 fibrogenetic effect Effects 0.000 claims description 2
239000011737 fluorine Substances 0.000 claims description 2
208000019622 heart disease Diseases 0.000 claims description 2
208000015181 infectious disease Diseases 0.000 claims description 2
239000011630 iodine Substances 0.000 claims description 2
208000028867 ischemia Diseases 0.000 claims description 2
ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 claims description 2
230000003211 malignant effect Effects 0.000 claims description 2
208000030159 metabolic disease Diseases 0.000 claims description 2
201000006417 multiple sclerosis Diseases 0.000 claims description 2
238000001959 radiotherapy Methods 0.000 claims description 2
229940124597 therapeutic agent Drugs 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims 3
QTFKWKHMQRDTEX-UHFFFAOYSA-N 1-[3-(azetidin-1-yl)phenyl]-3-cyclopropyl-5-(2-fluoro-4-iodoanilino)-6,8-dimethylpyrido[4,3-d]pyrimidine-2,4,7-trione Chemical compound O=C1N(C2CC2)C(=O)C2=C(NC=3C(=CC(I)=CC=3)F)N(C)C(=O)C(C)=C2N1C(C=1)=CC=CC=1N1CCC1 QTFKWKHMQRDTEX-UHFFFAOYSA-N 0.000 claims 2
KZEDEAZLGKBEQM-UHFFFAOYSA-N 3-cyclopropyl-5-(2-fluoro-4-iodoanilino)-1-[3-(3-hydroxyoxetan-3-yl)phenyl]-6,8-dimethylpyrido[4,3-d]pyrimidine-2,4,7-trione Chemical compound O=C1N(C2CC2)C(=O)C2=C(NC=3C(=CC(I)=CC=3)F)N(C)C(=O)C(C)=C2N1C(C=1)=CC=CC=1C1(O)COC1 KZEDEAZLGKBEQM-UHFFFAOYSA-N 0.000 claims 2
OVFDLSJZGPTDSD-UHFFFAOYSA-N 3-cyclopropyl-5-(2-fluoro-4-iodoanilino)-6,8-dimethyl-1-[3-(2-oxoazetidin-1-yl)phenyl]pyrido[4,3-d]pyrimidine-2,4,7-trione Chemical compound O=C1N(C2CC2)C(=O)C2=C(NC=3C(=CC(I)=CC=3)F)N(C)C(=O)C(C)=C2N1C(C=1)=CC=CC=1N1CCC1=O OVFDLSJZGPTDSD-UHFFFAOYSA-N 0.000 claims 2
JKPBUKGOABAHHL-UHFFFAOYSA-N 1-(3-cyclopropylsulfonylphenyl)-5-(2-fluoro-4-iodoanilino)-3,6,8-trimethylpyrido[4,3-d]pyrimidine-2,4,7-trione Chemical compound O=C1N(C)C(=O)C2=C(NC=3C(=CC(I)=CC=3)F)N(C)C(=O)C(C)=C2N1C(C=1)=CC=CC=1S(=O)(=O)C1CC1 JKPBUKGOABAHHL-UHFFFAOYSA-N 0.000 claims 1
VGGYBSBVXSFLEE-UHFFFAOYSA-N 1-(3-cyclopropylsulfonylphenyl)-5-(2-fluoro-4-iodoanilino)-6,8-dimethylpyrido[4,3-d]pyrimidine-2,4,7-trione Chemical compound O=C1NC(=O)C2=C(NC=3C(=CC(I)=CC=3)F)N(C)C(=O)C(C)=C2N1C(C=1)=CC=CC=1S(=O)(=O)C1CC1 VGGYBSBVXSFLEE-UHFFFAOYSA-N 0.000 claims 1
MICUMJRREWTXPP-UHFFFAOYSA-N 1-[3-(azetidin-1-yl)phenyl]-5-(2-fluoro-4-iodoanilino)-3,6,8-trimethylpyrido[4,3-d]pyrimidine-2,4,7-trione Chemical compound O=C1N(C)C(=O)C2=C(NC=3C(=CC(I)=CC=3)F)N(C)C(=O)C(C)=C2N1C(C=1)=CC=CC=1N1CCC1 MICUMJRREWTXPP-UHFFFAOYSA-N 0.000 claims 1
WWQPFZMFTXTVLU-UHFFFAOYSA-N 1-[3-(cyclopropanecarbonyl)phenyl]-3-cyclopropyl-5-(2-fluoro-4-iodoanilino)-6,8-dimethylpyrido[4,3-d]pyrimidine-2,4,7-trione Chemical compound O=C1N(C2CC2)C(=O)C2=C(NC=3C(=CC(I)=CC=3)F)N(C)C(=O)C(C)=C2N1C(C=1)=CC=CC=1C(=O)C1CC1 WWQPFZMFTXTVLU-UHFFFAOYSA-N 0.000 claims 1
LLLURJYEMVLZFC-UHFFFAOYSA-N 2-[1-[3-[5-(2-fluoro-4-iodoanilino)-3,6,8-trimethyl-2,4,7-trioxopyrido[4,3-d]pyrimidin-1-yl]phenyl]azetidin-3-yl]oxyacetamide Chemical compound O=C1N(C)C(=O)C2=C(NC=3C(=CC(I)=CC=3)F)N(C)C(=O)C(C)=C2N1C(C=1)=CC=CC=1N1CC(OCC(N)=O)C1 LLLURJYEMVLZFC-UHFFFAOYSA-N 0.000 claims 1
VWKZOIVWIMPNMS-UHFFFAOYSA-N 3-cyclopropyl-1-(3-cyclopropylsulfonylphenyl)-5-(2-fluoro-4-iodoanilino)-6,8-dimethylpyrido[4,3-d]pyrimidine-2,4,7-trione Chemical compound O=C1N(C2CC2)C(=O)C2=C(NC=3C(=CC(I)=CC=3)F)N(C)C(=O)C(C)=C2N1C(C=1)=CC=CC=1S(=O)(=O)C1CC1 VWKZOIVWIMPNMS-UHFFFAOYSA-N 0.000 claims 1
ZYCVEDVDIMHMDQ-UHFFFAOYSA-N 3-cyclopropyl-5-(2-fluoro-4-iodoanilino)-6,8-dimethyl-1-[3-(oxetan-3-ylamino)phenyl]pyrido[4,3-d]pyrimidine-2,4,7-trione Chemical compound O=C1N(C2CC2)C(=O)C2=C(NC=3C(=CC(I)=CC=3)F)N(C)C(=O)C(C)=C2N1C(C=1)=CC=CC=1NC1COC1 ZYCVEDVDIMHMDQ-UHFFFAOYSA-N 0.000 claims 1
ZMNFCBOTEZOZDX-UHFFFAOYSA-N 5-(2-fluoro-4-iodoanilino)-1-[3-(3-fluorooxetan-3-yl)phenyl]-3,6,8-trimethylpyrido[4,3-d]pyrimidine-2,4,7-trione Chemical compound O=C1N(C)C(=O)C2=C(NC=3C(=CC(I)=CC=3)F)N(C)C(=O)C(C)=C2N1C(C=1)=CC=CC=1C1(F)COC1 ZMNFCBOTEZOZDX-UHFFFAOYSA-N 0.000 claims 1
RHHKRZPZIMWRGZ-UHFFFAOYSA-N 5-(2-fluoro-4-iodoanilino)-1-[3-(3-hydroxyoxetan-3-yl)phenyl]-3,6,8-trimethylpyrido[4,3-d]pyrimidine-2,4,7-trione Chemical compound O=C1N(C)C(=O)C2=C(NC=3C(=CC(I)=CC=3)F)N(C)C(=O)C(C)=C2N1C(C=1)=CC=CC=1C1(O)COC1 RHHKRZPZIMWRGZ-UHFFFAOYSA-N 0.000 claims 1
MKZMOEHKSGBUFU-UHFFFAOYSA-N 5-(2-fluoro-4-iodoanilino)-3,6,8-trimethyl-1-[3-(oxetan-3-ylamino)phenyl]pyrido[4,3-d]pyrimidine-2,4,7-trione Chemical compound O=C1N(C)C(=O)C2=C(NC=3C(=CC(I)=CC=3)F)N(C)C(=O)C(C)=C2N1C(C=1)=CC=CC=1NC1COC1 MKZMOEHKSGBUFU-UHFFFAOYSA-N 0.000 claims 1
OLUSILLRZLWXOF-UHFFFAOYSA-N 5-(2-fluoro-4-iodoanilino)-3,6,8-trimethyl-1-[3-(oxetan-3-yloxy)phenyl]pyrido[4,3-d]pyrimidine-2,4,7-trione Chemical compound O=C1N(C)C(=O)C2=C(NC=3C(=CC(I)=CC=3)F)N(C)C(=O)C(C)=C2N1C(C=1)=CC=CC=1OC1COC1 OLUSILLRZLWXOF-UHFFFAOYSA-N 0.000 claims 1
LZKSNXWQOJKRJA-UHFFFAOYSA-N 5-(2-fluoro-4-iodoanilino)-3,6,8-trimethyl-1-[3-(oxetan-3-yloxymethyl)phenyl]pyrido[4,3-d]pyrimidine-2,4,7-trione Chemical compound O=C1N(C)C(=O)C2=C(NC=3C(=CC(I)=CC=3)F)N(C)C(=O)C(C)=C2N1C(C=1)=CC=CC=1COC1COC1 LZKSNXWQOJKRJA-UHFFFAOYSA-N 0.000 claims 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

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- A61K31/541—Non-condensed thiazines containing further heterocyclic rings
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Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Organic Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Bioinformatics & Cheminformatics (AREA)
Epidemiology (AREA)
Immunology (AREA)
Biomedical Technology (AREA)
Oncology (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Hematology (AREA)
Heart & Thoracic Surgery (AREA)
Communicable Diseases (AREA)
Rheumatology (AREA)
Cardiology (AREA)
Physical Education & Sports Medicine (AREA)
Radiology & Medical Imaging (AREA)
Pathology (AREA)
Diabetes (AREA)
Pulmonology (AREA)
Urology & Nephrology (AREA)
Obesity (AREA)
Hospice & Palliative Care (AREA)
Orthopedic Medicine & Surgery (AREA)
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Psychiatry (AREA)
Transplantation (AREA)
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CA2865167A 2012-03-14 2013-03-11 Heterocyclyl compounds Expired - Fee Related CA2865167C (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
IN288/KOL/2012		2012-03-14
IN288KO2012		2012-03-14
PCT/IB2013/051915 WO2013136254A1 (en)	2012-03-14	2013-03-11	Heterocyclyl compounds

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CN (4)	CN108383836B (2)
AP (2)	AP3859A (2)
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AP2014008009A0 (en)	2014-10-31
DK2834237T3 (en)	2018-08-27
UA114906C2 (uk)	2017-08-28
EA028232B1 (ru)	2017-10-31
EP2834237B1 (en)	2018-06-06
JP6431770B2 (ja)	2018-11-28
US9428499B2 (en)	2016-08-30
KR20190073597A (ko)	2019-06-26
IL234560A (en)	2017-06-29
WO2013136254A1 (en)	2013-09-19
AU2018202568A1 (en)	2018-05-10
IN2014MN01755A (2)	2015-07-03
AP3859A (en)	2016-10-31
US20150133424A1 (en)	2015-05-14
NZ629432A (en)	2017-01-27
KR20140138911A (ko)	2014-12-04
CU20140110A7 (es)	2014-11-27
EP2834237A1 (en)	2015-02-11
CN108383836B (zh)	2021-11-12
HK1206020A1 (en)	2015-12-31
CN104271577A (zh)	2015-01-07
MA37400A1 (fr)	2016-05-31
MX2014010925A (es)	2015-04-10
CU24335B1 (es)	2018-04-03
CL2014002411A1 (es)	2015-04-06
US9969731B2 (en)	2018-05-15
US20160331753A1 (en)	2016-11-17
NZ629442A (en)	2016-12-23
PE20141973A1 (es)	2014-12-12
US9827247B2 (en)	2017-11-28
PH12014502041A1 (en)	2014-11-24
PL2834237T3 (pl)	2018-11-30
US20170101408A1 (en)	2017-04-13
DOP2014000203A (es)	2015-02-15
UA114907C2 (uk)	2017-08-28
CR20140463A (es)	2014-11-28
HK1202538A1 (en)	2015-10-02
ZA201406186B (en)	2016-06-29
SG11201405007QA (en)	2014-10-30
JP2018115215A (ja)	2018-07-26
JP2015509975A (ja)	2015-04-02
AU2017200493B2 (en)	2018-03-29
SG11201405006PA (en)	2014-10-30
GT201400195A (es)	2017-11-09
CA2865164C (en)	2021-06-08
IN2014MN01754A (2)	2015-07-03
DOP2014000204A (es)	2015-02-15
ES2741896T3 (es)	2020-02-12
MX355474B (es)	2018-04-16
AU2013234009B2 (en)	2016-10-27
KR20190100472A (ko)	2019-08-28
GT201400196A (es)	2017-09-28
MX2014010928A (es)	2015-04-10
AU2017200493A1 (en)	2017-02-16
EP2834236A1 (en)	2015-02-11
TR201811976T4 (tr)	2018-09-21
PE20141974A1 (es)	2014-12-12
CN108383836A (zh)	2018-08-10
NI201400108A (es)	2014-11-28
PH12014502040A1 (en)	2014-11-24
CR20140464A (es)	2014-11-28
BR112014022713A2 (2)	2017-06-20
US9555035B2 (en)	2017-01-31
CO7160029A2 (es)	2015-01-15
EA201491672A1 (ru)	2014-12-30
CA2865164A1 (en)	2013-09-19
EP2834236B1 (en)	2019-05-22
TN2014000357A1 (en)	2015-12-21
AU2013234009A1 (en)	2014-09-25
EA201491671A1 (ru)	2014-12-30
CO7170131A2 (es)	2015-01-28
NI201400107A (es)	2014-11-26
MX366426B (es)	2019-07-08
CA2865167A1 (en)	2013-09-19
CL2014002412A1 (es)	2015-03-06
GEP201706671B (en)	2017-05-25
MY174188A (en)	2020-03-12
AU2018202568B2 (en)	2019-05-09
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HK1206020B (en)	2020-01-24	Heterocyclyl compounds
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OA17318A (en)	2016-05-23	Heterocyclyl Compounds.
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