HRP20100446T1 - Derivat tieno[3,2-d]pirimidina koristan kao inhibitor pi3k - Google Patents

Derivat tieno[3,2-d]pirimidina koristan kao inhibitor pi3k Download PDF

Info

Publication number: HRP20100446T1
Authority: HR; Croatia
Prior art keywords: acid; compound; cancer; carcinoma; treatment
Prior art date: 2006-04-26

Application number

HR20100446T

Other languages

English (en)

Croatian (hr)

Inventor

Chuckowree Irina

Folkes Adrian

Hancox Tim

Shuttleworth Stephen

Original Assignee

F. Hoffmann-La Roche Ag

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.)

2006-04-26

Filing date

2010-08-10

Publication date

2010-09-30

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=38645682&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=HRP20100446(T1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

2010-08-10 Application filed by F. Hoffmann-La Roche Ag filed Critical F. Hoffmann-La Roche Ag

2010-09-30 Publication of HRP20100446T1 publication Critical patent/HRP20100446T1/hr

Links

RBNBDIMXFJYDLQ-UHFFFAOYSA-N thieno[3,2-d]pyrimidine Chemical class C1=NC=C2SC=CC2=N1 RBNBDIMXFJYDLQ-UHFFFAOYSA-N 0.000 title claims abstract 3
239000012828 PI3K inhibitor Substances 0.000 title 1
229940043441 phosphoinositide 3-kinase inhibitor Drugs 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract 23
150000003839 salts Chemical class 0.000 claims abstract 6
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 9
206010028980 Neoplasm Diseases 0.000 claims 8
208000035475 disorder Diseases 0.000 claims 6
201000011510 cancer Diseases 0.000 claims 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 4
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 4
238000000034 method Methods 0.000 claims 4
239000000825 pharmaceutical preparation Substances 0.000 claims 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims 3
210000001072 colon Anatomy 0.000 claims 3
201000010099 disease Diseases 0.000 claims 3
206010009944 Colon cancer Diseases 0.000 claims 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 2
206010029260 Neuroblastoma Diseases 0.000 claims 2
102000003993 Phosphatidylinositol 3-kinases Human genes 0.000 claims 2
108090000430 Phosphatidylinositol 3-kinases Proteins 0.000 claims 2
208000024770 Thyroid neoplasm Diseases 0.000 claims 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 2
239000002253 acid Substances 0.000 claims 2
229910000147 aluminium phosphate Inorganic materials 0.000 claims 2
230000006399 behavior Effects 0.000 claims 2
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims 2
229940092714 benzenesulfonic acid Drugs 0.000 claims 2
230000003915 cell function Effects 0.000 claims 2
230000010261 cell growth Effects 0.000 claims 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 2
150000002148 esters Chemical class 0.000 claims 2
208000005017 glioblastoma Diseases 0.000 claims 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims 2
210000004185 liver Anatomy 0.000 claims 2
238000004519 manufacturing process Methods 0.000 claims 2
201000001441 melanoma Diseases 0.000 claims 2
229940098779 methanesulfonic acid Drugs 0.000 claims 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 2
210000000214 mouth Anatomy 0.000 claims 2
208000002154 non-small cell lung carcinoma Diseases 0.000 claims 2
210000003800 pharynx Anatomy 0.000 claims 2
229960004838 phosphoric acid Drugs 0.000 claims 2
210000002307 prostate Anatomy 0.000 claims 2
229940032330 sulfuric acid Drugs 0.000 claims 2
230000001225 therapeutic effect Effects 0.000 claims 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 2
208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims 1
RFRIKACSFOTIMU-UHFFFAOYSA-N 4-[2-(1h-indazol-4-yl)-6-[(4-methylsulfonylpiperazin-1-yl)methyl]thieno[3,2-d]pyrimidin-4-yl]morpholine;methanesulfonic acid Chemical compound CS(O)(=O)=O.CS(O)(=O)=O.C1CN(S(=O)(=O)C)CCN1CC1=CC2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2S1 RFRIKACSFOTIMU-UHFFFAOYSA-N 0.000 claims 1
208000010507 Adenocarcinoma of Lung Diseases 0.000 claims 1
208000003200 Adenoma Diseases 0.000 claims 1
206010001233 Adenoma benign Diseases 0.000 claims 1
206010004593 Bile duct cancer Diseases 0.000 claims 1
206010005003 Bladder cancer Diseases 0.000 claims 1
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims 1
201000009030 Carcinoma Diseases 0.000 claims 1
208000010667 Carcinoma of liver and intrahepatic biliary tract Diseases 0.000 claims 1
208000024172 Cardiovascular disease Diseases 0.000 claims 1
208000001333 Colorectal Neoplasms Diseases 0.000 claims 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 1
206010014759 Endometrial neoplasm Diseases 0.000 claims 1
206010061968 Gastric neoplasm Diseases 0.000 claims 1
WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims 1
206010073069 Hepatic cancer Diseases 0.000 claims 1
206010061218 Inflammation Diseases 0.000 claims 1
206010023347 Keratoacanthoma Diseases 0.000 claims 1
208000008839 Kidney Neoplasms Diseases 0.000 claims 1
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims 1
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims 1
206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
208000012902 Nervous system disease Diseases 0.000 claims 1
208000025966 Neurological disease Diseases 0.000 claims 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims 1
208000000236 Prostatic Neoplasms Diseases 0.000 claims 1
208000015634 Rectal Neoplasms Diseases 0.000 claims 1
206010038389 Renal cancer Diseases 0.000 claims 1
206010039491 Sarcoma Diseases 0.000 claims 1
201000010208 Seminoma Diseases 0.000 claims 1
208000000453 Skin Neoplasms Diseases 0.000 claims 1
208000005718 Stomach Neoplasms Diseases 0.000 claims 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims 1
208000033781 Thyroid carcinoma Diseases 0.000 claims 1
208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims 1
208000036142 Viral infection Diseases 0.000 claims 1
230000002159 abnormal effect Effects 0.000 claims 1
229960000583 acetic acid Drugs 0.000 claims 1
150000007513 acids Chemical class 0.000 claims 1
239000013543 active substance Substances 0.000 claims 1
208000009956 adenocarcinoma Diseases 0.000 claims 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims 1
150000001412 amines Chemical class 0.000 claims 1
235000003704 aspartic acid Nutrition 0.000 claims 1
OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims 1
201000007180 bile duct carcinoma Diseases 0.000 claims 1
201000001531 bladder carcinoma Diseases 0.000 claims 1
201000004571 bone carcinoma Diseases 0.000 claims 1
KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims 1
239000004327 boric acid Substances 0.000 claims 1
229910052796 boron Inorganic materials 0.000 claims 1
210000004556 brain Anatomy 0.000 claims 1
201000000220 brain stem cancer Diseases 0.000 claims 1
210000000481 breast Anatomy 0.000 claims 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims 1
239000003054 catalyst Substances 0.000 claims 1
201000007455 central nervous system cancer Diseases 0.000 claims 1
239000003638 chemical reducing agent Substances 0.000 claims 1
235000015165 citric acid Nutrition 0.000 claims 1
208000029742 colonic neoplasm Diseases 0.000 claims 1
239000003085 diluting agent Substances 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
230000000694 effects Effects 0.000 claims 1
230000007368 endocrine function Effects 0.000 claims 1
210000004696 endometrium Anatomy 0.000 claims 1
210000003238 esophagus Anatomy 0.000 claims 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 claims 1
208000021045 exocrine pancreatic carcinoma Diseases 0.000 claims 1
235000019253 formic acid Nutrition 0.000 claims 1
229940013688 formic acid Drugs 0.000 claims 1
239000001530 fumaric acid Substances 0.000 claims 1
206010017758 gastric cancer Diseases 0.000 claims 1
235000013922 glutamic acid Nutrition 0.000 claims 1
239000004220 glutamic acid Substances 0.000 claims 1
210000003128 head Anatomy 0.000 claims 1
206010073071 hepatocellular carcinoma Diseases 0.000 claims 1
229960000443 hydrochloric acid Drugs 0.000 claims 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims 1
229940071870 hydroiodic acid Drugs 0.000 claims 1
208000026278 immune system disease Diseases 0.000 claims 1
230000004054 inflammatory process Effects 0.000 claims 1
201000010982 kidney cancer Diseases 0.000 claims 1
239000004310 lactic acid Substances 0.000 claims 1
235000014655 lactic acid Nutrition 0.000 claims 1
210000000867 larynx Anatomy 0.000 claims 1
208000032839 leukemia Diseases 0.000 claims 1
210000000088 lip Anatomy 0.000 claims 1
201000002250 liver carcinoma Diseases 0.000 claims 1
208000014018 liver neoplasm Diseases 0.000 claims 1
210000004072 lung Anatomy 0.000 claims 1
201000005249 lung adenocarcinoma Diseases 0.000 claims 1
201000005202 lung cancer Diseases 0.000 claims 1
208000020816 lung neoplasm Diseases 0.000 claims 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 1
239000011976 maleic acid Substances 0.000 claims 1
239000001630 malic acid Substances 0.000 claims 1
235000011090 malic acid Nutrition 0.000 claims 1
230000007102 metabolic function Effects 0.000 claims 1
210000003739 neck Anatomy 0.000 claims 1
229940074355 nitric acid Drugs 0.000 claims 1
229910017604 nitric acid Inorganic materials 0.000 claims 1
210000001672 ovary Anatomy 0.000 claims 1
235000006408 oxalic acid Nutrition 0.000 claims 1
208000008443 pancreatic carcinoma Diseases 0.000 claims 1
201000010198 papillary carcinoma Diseases 0.000 claims 1
239000008194 pharmaceutical composition Substances 0.000 claims 1
230000000069 prophylactic effect Effects 0.000 claims 1
235000019260 propionic acid Nutrition 0.000 claims 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims 1
206010038038 rectal cancer Diseases 0.000 claims 1
201000001275 rectum cancer Diseases 0.000 claims 1
201000000849 skin cancer Diseases 0.000 claims 1
208000000649 small cell carcinoma Diseases 0.000 claims 1
210000000813 small intestine Anatomy 0.000 claims 1
239000002904 solvent Substances 0.000 claims 1
210000002784 stomach Anatomy 0.000 claims 1
201000011549 stomach cancer Diseases 0.000 claims 1
239000011975 tartaric acid Substances 0.000 claims 1
235000002906 tartaric acid Nutrition 0.000 claims 1
210000001550 testis Anatomy 0.000 claims 1
201000002510 thyroid cancer Diseases 0.000 claims 1
208000013077 thyroid gland carcinoma Diseases 0.000 claims 1
208000030901 thyroid gland follicular carcinoma Diseases 0.000 claims 1
210000002105 tongue Anatomy 0.000 claims 1
208000010576 undifferentiated carcinoma Diseases 0.000 claims 1
208000010570 urinary bladder carcinoma Diseases 0.000 claims 1
230000009385 viral infection Effects 0.000 claims 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5355—Non-condensed oxazines and containing further heterocyclic rings
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- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
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HR20100446T 2006-04-26 2010-08-10 Derivat tieno[3,2-d]pirimidina koristan kao inhibitor pi3k HRP20100446T1 (hr)

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US79496606P	2006-04-26	2006-04-26
PCT/IB2007/001058 WO2007129161A2 (en)	2006-04-26	2007-04-24	Thieno [3, 2-d] pyrimidine derivative useful as pi3k inhibitor

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MX2008013578A (es)	2009-03-23
US7781433B2 (en)	2010-08-24
AU2007246793A1 (en)	2007-11-15
JP2009534461A (ja)	2009-09-24
BRPI0710874A2 (pt)	2012-02-14
JP5148597B2 (ja)	2013-02-20
NZ572812A (en)	2010-09-30
UA95799C2 (en)	2011-09-12
US8987260B2 (en)	2015-03-24
CN101472930B (zh)	2011-12-14
KR20090021156A (ko)	2009-02-27
IL194784A0 (en)	2009-08-03
MA30412B1 (fr)	2009-05-04
AU2007246793B2 (en)	2013-02-07
CL2007001165A1 (es)	2008-01-25
HK1127477A1 (en)	2009-09-25
CA2650303C (en)	2015-03-24
US20140221367A1 (en)	2014-08-07
NO342593B1 (no)	2018-06-18
TWI409268B (zh)	2013-09-21
KR101533461B1 (ko)	2015-07-02
CN101472930A (zh)	2009-07-01
US20080076768A1 (en)	2008-03-27
ES2347187T3 (es)	2010-10-26
ATE471940T1 (de)	2010-07-15
ECSP088913A (es)	2008-12-30
MY145306A (en)	2012-01-13
CA2650303A1 (en)	2007-11-15
US8685968B2 (en)	2014-04-01
DE602007007323D1 (de)	2010-08-05
IL194784A (en)	2014-03-31
DK2024372T3 (da)	2010-09-20
RU2439074C2 (ru)	2012-01-10
RU2008145663A (ru)	2010-06-20
US20110065701A1 (en)	2011-03-17
US8324206B2 (en)	2012-12-04
ZA200809967B (en)	2009-08-26
US20130230585A1 (en)	2013-09-05
WO2007129161A3 (en)	2008-01-24
WO2007129161A2 (en)	2007-11-15
TW200811188A (en)	2008-03-01
NO20084931L (no)	2009-01-16
PT2024372E (pt)	2010-09-16
AR060631A1 (es)	2008-07-02
RS51401B (en)	2011-02-28
CR10455A (es)	2009-01-27

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