JP2011527686A5 - - Google Patents
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- JP2011527686A5 JP2011527686A5 JP2011517520A JP2011517520A JP2011527686A5 JP 2011527686 A5 JP2011527686 A5 JP 2011527686A5 JP 2011517520 A JP2011517520 A JP 2011517520A JP 2011517520 A JP2011517520 A JP 2011517520A JP 2011527686 A5 JP2011527686 A5 JP 2011527686A5
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- oxadiazole
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- 150000001875 compounds Chemical class 0.000 claims 77
- 150000003839 salts Chemical class 0.000 claims 48
- 239000011780 sodium chloride Substances 0.000 claims 48
- -1 3-bromo-4-fluorophenyl Chemical group 0.000 claims 14
- 239000008194 pharmaceutical composition Substances 0.000 claims 9
- 239000007787 solid Substances 0.000 claims 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 5
- 239000003153 chemical reaction reagent Substances 0.000 claims 4
- 238000000034 method Methods 0.000 claims 4
- 150000007530 organic bases Chemical class 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 238000000634 powder X-ray diffraction Methods 0.000 claims 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 4
- 150000001412 amines Chemical class 0.000 claims 3
- 239000002246 antineoplastic agent Substances 0.000 claims 3
- 239000012351 deprotecting agent Substances 0.000 claims 3
- 238000002560 therapeutic procedure Methods 0.000 claims 3
- 229960005486 vaccines Drugs 0.000 claims 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- NVBFHJWHLNUMCV-UHFFFAOYSA-N Sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 claims 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 2
- 150000001408 amides Chemical group 0.000 claims 2
- 230000000259 anti-tumor Effects 0.000 claims 2
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 2
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide Chemical compound [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims 2
- 230000002401 inhibitory effect Effects 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 206010003816 Autoimmune disease Diseases 0.000 claims 1
- 210000004556 Brain Anatomy 0.000 claims 1
- 210000000481 Breast Anatomy 0.000 claims 1
- YHEQSGUVCLJBDT-UHFFFAOYSA-N CS(=O)(=O)NCCCNC1=NON=C1C(=NO)NC1=CC=C(F)C(C(F)(F)F)=C1 Chemical compound CS(=O)(=O)NCCCNC1=NON=C1C(=NO)NC1=CC=C(F)C(C(F)(F)F)=C1 YHEQSGUVCLJBDT-UHFFFAOYSA-N 0.000 claims 1
- GHLDPOHYOPWBDC-UHFFFAOYSA-N CS(=O)(=O)NCCNC1=NON=C1C(=NO)NC1=CC=C(F)C(C#N)=C1 Chemical compound CS(=O)(=O)NCCNC1=NON=C1C(=NO)NC1=CC=C(F)C(C#N)=C1 GHLDPOHYOPWBDC-UHFFFAOYSA-N 0.000 claims 1
- 208000002177 Cataract Diseases 0.000 claims 1
- 210000003679 Cervix Uteri Anatomy 0.000 claims 1
- 210000001072 Colon Anatomy 0.000 claims 1
- 206010062016 Immunosuppression Diseases 0.000 claims 1
- 206010022114 Injury Diseases 0.000 claims 1
- 210000003734 Kidney Anatomy 0.000 claims 1
- 206010024324 Leukaemias Diseases 0.000 claims 1
- 210000004072 Lung Anatomy 0.000 claims 1
- 206010025323 Lymphomas Diseases 0.000 claims 1
- 206010025650 Malignant melanoma Diseases 0.000 claims 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N Methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 claims 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 claims 1
- QSSITYLVAQOWSO-UHFFFAOYSA-N N-[2-[[4-[[4-fluoro-3-(trifluoromethyl)anilino]-nitrosomethylidene]-1,2,5-oxadiazol-3-yl]amino]ethyl]methanesulfonamide Chemical compound CS(=O)(=O)NCCNC1=NONC1=C(N=O)NC1=CC=C(F)C(C(F)(F)F)=C1 QSSITYLVAQOWSO-UHFFFAOYSA-N 0.000 claims 1
- HMNCIHXNFCSJKK-UHFFFAOYSA-N NS(=O)(=O)NCCCNC1=NON=C1C(=NO)NC1=CC=C(F)C(C(F)(F)F)=C1 Chemical compound NS(=O)(=O)NCCCNC1=NON=C1C(=NO)NC1=CC=C(F)C(C(F)(F)F)=C1 HMNCIHXNFCSJKK-UHFFFAOYSA-N 0.000 claims 1
- JIVHKHGOKPSNGR-UHFFFAOYSA-N NS(=O)(=O)NCCNC1=NON=C1C(=NO)NC1=CC=C(F)C(C(F)(F)F)=C1 Chemical compound NS(=O)(=O)NCCNC1=NON=C1C(=NO)NC1=CC=C(F)C(C(F)(F)F)=C1 JIVHKHGOKPSNGR-UHFFFAOYSA-N 0.000 claims 1
- 206010053643 Neurodegenerative disease Diseases 0.000 claims 1
- 206010025310 Other lymphomas Diseases 0.000 claims 1
- 210000001672 Ovary Anatomy 0.000 claims 1
- 210000000496 Pancreas Anatomy 0.000 claims 1
- 210000002307 Prostate Anatomy 0.000 claims 1
- 210000001550 Testis Anatomy 0.000 claims 1
- 206010052779 Transplant rejections Diseases 0.000 claims 1
- 206010047461 Viral infection Diseases 0.000 claims 1
- 208000001756 Virus Disease Diseases 0.000 claims 1
- 230000032683 aging Effects 0.000 claims 1
- 230000001093 anti-cancer Effects 0.000 claims 1
- 230000000840 anti-viral Effects 0.000 claims 1
- 102000004965 antibodies Human genes 0.000 claims 1
- 108090001123 antibodies Proteins 0.000 claims 1
- 239000003443 antiviral agent Substances 0.000 claims 1
- 201000009596 autoimmune hypersensitivity disease Diseases 0.000 claims 1
- 238000009566 cancer vaccine Methods 0.000 claims 1
- 230000001808 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- 239000002254 cytotoxic agent Substances 0.000 claims 1
- 231100000599 cytotoxic agent Toxicity 0.000 claims 1
- 238000001938 differential scanning calorimetry curve Methods 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 201000010536 head and neck cancer Diseases 0.000 claims 1
- 230000001506 immunosuppresive Effects 0.000 claims 1
- 239000003018 immunosuppressive agent Substances 0.000 claims 1
- 102000006639 indoleamine 2,3-dioxygenase family Human genes 0.000 claims 1
- 108020004201 indoleamine 2,3-dioxygenase family Proteins 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 201000001441 melanoma Diseases 0.000 claims 1
- 238000002844 melting Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 claims 1
- 210000000056 organs Anatomy 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 239000003223 protective agent Substances 0.000 claims 1
- 239000005483 tyrosine kinase inhibitor Substances 0.000 claims 1
- 150000004917 tyrosine kinase inhibitor derivatives Chemical class 0.000 claims 1
- 229940121358 tyrosine kinase inhibitors Drugs 0.000 claims 1
- 230000017613 viral reproduction Effects 0.000 claims 1
- 0 C*(C*(C)Nc1n[o]nc1C(N1c2ccc(*)c(*)c2)=NOC1=O)CNS(*)(=O)=O Chemical compound C*(C*(C)Nc1n[o]nc1C(N1c2ccc(*)c(*)c2)=NOC1=O)CNS(*)(=O)=O 0.000 description 2
Claims (49)
- R1はNH2である、請求項1に記載の化合物、またはその医薬的に許容される塩。
- R1はCH3である、請求項1に記載の化合物、またはその医薬的に許容される塩。
- R2はClである、請求項1〜3のうちのいずれか1項に記載の化合物、またはその医薬的に許容される塩。
- R2はBrである、請求項1〜3のうちのいずれか1項に記載の化合物、またはその医薬的に許容される塩。
- R2はCF3である、請求項1〜3のうちのいずれか1項に記載の化合物、またはその医薬的に許容される塩。
- R2はCH3である、請求項1〜3のうちのいずれか1項に記載の化合物、またはその医薬的に許容される塩。
- R2はCNである、請求項1〜3のうちのいずれか1項に記載の化合物、またはその医薬的に許容される塩。
- R3はHである、請求項1〜8のうちのいずれか1項に記載の化合物、またはその医薬的に許容される塩。
- R3はFである、請求項1〜8のうちのいずれか1項に記載の化合物、またはその医薬的に許容される塩。
- nは1である、請求項1〜10のうちのいずれか1項に記載の化合物、またはその医薬的に許容される塩。
- nは2である、請求項1〜10のうちのいずれか1項に記載の化合物、またはその医薬的に許容される塩。
- 4−({2−[(アミノスルホニル)アミノ]エチル}アミノ)−N−(3−ブロモ−4−フルオロフェニル)−N’−ヒドロキシ−1,2,5−オキサジアゾール−3−カルボキシミドアミド、
N−(3−ブロモ−4−フルオロフェニル)−N’−ヒドロキシ−4−({2−[(メチルスルホニル)アミノ]エチル}アミノ)−1,2,5−オキサジアゾール−3−カルボキシミドアミド、
4−({3−[(アミノスルホニル)アミノ]プロピル}アミノ)−N−(3−ブロモ−4−フルオロフェニル)−N’−ヒドロキシ−1,2,5−オキサジアゾール−3−カルボキシミドアミド、
N−(3−ブロモ−4−フルオロフェニル)−N’−ヒドロキシ−4−({3−[(メチルスルホニル)アミノ]プロピル}アミノ)−1,2,5−オキサジアゾール−3−カルボキシミドアミド、
4−({2−[(アミノスルホニル)アミノ]エチル}アミノ)−N−(3−クロロ−4−フルオロフェニル)−N’−ヒドロキシ−1,2,5−オキサジアゾール−3−カルボキシミドアミド、
N−(3−クロロ−4−フルオロフェニル)−N’−ヒドロキシ−4−({2−[(メチルスルホニル)アミノ]エチル}アミノ)−1,2,5−オキサジアゾール−3−カルボキシミドアミド、
4−({3−[(アミノスルホニル)アミノ]プロピル}アミノ)−N−(3−クロロ−4−フルオロフェニル)−N’−ヒドロキシ−1,2,5−オキサジアゾール−3−カルボキシミドアミド、
N−(3−クロロ−4−フルオロフェニル)−N’−ヒドロキシ−4−({3−[(メチルスルホニル)アミノ]プロピル}アミノ)−1,2,5−オキサジアゾール−3−カルボキシミドアミド、
4−({2−[(アミノスルホニル)アミノ]エチル}アミノ)−N−[4−フルオロ−3−(トリフルオロメチル)フェニル]−N’−ヒドロキシ−1,2,5−オキサジアゾール−3−カルボキシミドアミド、
N−[4−フルオロ−3−(トリフルオロメチル)フェニル]−N’−ヒドロキシ−4−({2−[(メチルスルホニル)アミノ]エチル}−アミノ)−1,2,5−オキサジアゾール−3−カルボキシミドアミド、
4−({3−[(アミノスルホニル)アミノ]プロピル}アミノ)−N−[4−フルオロ−3−(トリフルオロメチル)フェニル]−N’−ヒドロキシ−1,2,5−オキサジアゾール−3−カルボキシミドアミド、
N−[4−フルオロ−3−(トリフルオロメチル)フェニル]−N’−ヒドロキシ−4−({3−[(メチルスルホニル)アミノ]プロピル}−アミノ)−1,2,5−オキサジアゾール−3−カルボキシミドアミド、
4−({2−[(アミノスルホニル)アミノ]エチル}アミノ)−N’−ヒドロキシ−N−[3−(トリフルオロメチル)フェニル]−1,2,5−オキサジアゾール−3−カルボキシミドアミド、
N’−ヒドロキシ−4−({2−[(メチルスルホニル)アミノ]エチル}アミノ)−N−[3−(トリフルオロメチル)フェニル]−1,2,5−オキサジアゾール−3−カルボキシミドアミド、
4−({3−[(アミノスルホニル)アミノ]プロピル}アミノ)−N’−ヒドロキシ−N−[3−(トリフルオロメチル)フェニル]−1,2,5−オキサジアゾール−3−カルボキシミドアミド、
N’−ヒドロキシ−4−({3−[(メチルスルホニル)アミノ]プロピル}アミノ)−N−[3−(トリフルオロメチル)フェニル]−1,2,5−オキサジアゾール−3−カルボキシミドアミド、
N−(4−フルオロ−3−メチルフェニル)−N’−ヒドロキシ−4−({2−[(メチルスルホニル)アミノ]エチル}アミノ)−1,2,5−オキサジアゾール−3−カルボキシミドアミド、
4−({2−[(アミノスルホニル)アミノ]エチル}アミノ)−N−(3−シアノ−4−フルオロフェニル)−N’−ヒドロキシ−1,2,5−オキサジアゾール−3−カルボキシミドアミド、および
N−(3−シアノ−4−フルオロフェニル)−N’−ヒドロキシ−4−({2−[(メチルスルホニル)アミノ]エチル}アミノ)−1,2,5−オキサジアゾール−3−カルボキシミドアミド、
から選択される、請求項1に記載の化合物、またはその医薬的に許容される塩。 - 4−({2−[(アミノスルホニル)アミノ]エチル}アミノ)−N−(3−ブロモ−4−フルオロフェニル)−N’−ヒドロキシ−1,2,5−オキサジアゾール−3−カルボキシミドアミドである化合物、またはその医薬的に許容される塩。
- 4−({2−[(アミノスルホニル)アミノ]エチル}アミノ)−N−(3−ブロモ−4−フルオロフェニル)−N’−ヒドロキシ−1,2,5−オキサジアゾール−3−カルボキシミドアミドである化合物。
- 結晶性である、請求項15に記載の化合物の固体。
- 実質的に無水である、請求項15に記載の化合物の固体。
- 約162〜約166℃の融点を有する、請求項15に記載の化合物の固体。
- 実質的に図2に示されるようなDSCサーモグラムを有する、請求項15に記載の化合物の固体。
- 2シータでの約18.4°、約18.9°、約21.8°、約23.9°、約29.2°、および約38.7°から選択される、少なくとも1つのXRPDピークを有する、請求項15に記載の化合物の固体。
- 2シータでの約18.4°、約18.9°、約21.8°、約23.9°、約29.2°、および約38.7°から選択される、少なくとも2つのXRPDピークを有する、請求項15に記載の化合物の固体。
- 2シータでの約18.4°、約18.9°、約21.8°、約23.9°、約29.2°、および約38.7°から選択される、少なくとも3つのXRPDピークを有する、請求項15に記載の化合物の固体。
- 実質的に図1に示されるようなXRPDパターンを有する、請求項15に記載の化合物の固体。
- 4−({2−[(アミノスルホニル)アミノ]エチル}アミノ)−N−[(4−ブロモ−2−フリル)メチル]−N’−ヒドロキシ−1,2,5−オキサジアゾール−3−カルボキシミドアミドである化合物、またはその医薬的に許容される塩。
- 4−({2−[(アミノスルホニル)アミノ]エチル}アミノ)−N−[(4−クロロ−2−フリル)メチル]−N’−ヒドロキシ−1,2,5−オキサジアゾール−3−カルボキシミドアミドである化合物、またはその医薬的に許容される塩。
- 請求項1〜15および24〜26のうちのいずれか1項に記載の化合物、またはその医薬的に許容される塩、および少なくとも1つの医薬的に許容される担体を含む、組成物。
- 請求項1〜15および24〜26のうちのいずれか1項に記載の化合物、またはその医薬的に許容される塩を含む、インドールアミン2,3−ジオキシゲナーゼの活性を阻害するための医薬組成物。
- 請求項1〜15および24〜26のうちのいずれか1項に記載の化合物、またはその医薬的に許容される塩を含む、患者における免疫抑制を阻害するための医薬組成物。
- 請求項1〜15および24〜26のうちのいずれか1項に記載の化合物、またはその医薬的に許容される塩を含む、患者における癌、ウイルス感染、鬱病、神経変性疾患、外傷、加齢に伴う白内障、臓器移植拒絶反応、または自己免疫疾患を治療するための医薬組成物。
- 癌が、結腸、膵臓、乳房、前立腺、肺、脳、卵巣、子宮頸、睾丸、腎臓、頭部および頸部の癌、リンパ腫、および白血病から選択される、請求項30に記載の医薬組成物。
- 抗癌ワクチン、抗CTLA4抗体、抗ウイルス薬、化学療法薬、免疫抑制剤、放射線、抗腫瘍ワクチン、抗ウイルス性ワクチン、サイトカイン療法、またはチロシンキナーゼ阻害剤をさらに含む、請求項30に記載の医薬組成物。
- サイトカイン療法がIL2を含む、請求項32に記載の医薬組成物。
- 化学療法薬が細胞毒性薬である、請求項32に記載の医薬組成物。
- 請求項1〜15および24〜26のうちのいずれか1項に記載の化合物、またはその医薬的に許容される塩を含む、患者における黒色腫を治療するための医薬組成物。
- 化学療法薬、放射線、抗腫瘍ワクチン、またはサイトカイン療法をさらに含む、請求項35に記載の医薬組成物。
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US7887608P | 2008-07-08 | 2008-07-08 | |
US61/078,876 | 2008-07-08 | ||
US15087309P | 2009-02-09 | 2009-02-09 | |
US61/150,873 | 2009-02-09 | ||
PCT/US2009/049794 WO2010005958A2 (en) | 2008-07-08 | 2009-07-07 | 1,2,5-oxadiazoles as inhibitors of indoleamine 2,3-dioxygenase |
Related Child Applications (1)
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JP2014009612A Division JP5819451B2 (ja) | 2008-07-08 | 2014-01-22 | インドールアミン2,3−ジオキシゲナーゼの阻害剤としての1,2,5−オキサジアゾール |
Publications (3)
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JP2011527686A JP2011527686A (ja) | 2011-11-04 |
JP2011527686A5 true JP2011527686A5 (ja) | 2012-08-23 |
JP5465720B2 JP5465720B2 (ja) | 2014-04-09 |
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JP2011517520A Active JP5465720B2 (ja) | 2008-07-08 | 2009-07-07 | インドールアミン2,3−ジオキシゲナーゼの阻害剤としての1,2,5−オキサジアゾール |
JP2014009612A Active JP5819451B2 (ja) | 2008-07-08 | 2014-01-22 | インドールアミン2,3−ジオキシゲナーゼの阻害剤としての1,2,5−オキサジアゾール |
Family Applications After (1)
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JP2014009612A Active JP5819451B2 (ja) | 2008-07-08 | 2014-01-22 | インドールアミン2,3−ジオキシゲナーゼの阻害剤としての1,2,5−オキサジアゾール |
Country Status (37)
Country | Link |
---|---|
US (11) | US8088803B2 (ja) |
EP (3) | EP2824100B1 (ja) |
JP (2) | JP5465720B2 (ja) |
KR (5) | KR102031538B1 (ja) |
CN (2) | CN102164902B (ja) |
AR (1) | AR072490A1 (ja) |
AU (6) | AU2009268739B2 (ja) |
BR (2) | BRPI0915692B8 (ja) |
CA (2) | CA3012229C (ja) |
CL (2) | CL2009001554A1 (ja) |
CO (1) | CO6341622A2 (ja) |
CR (1) | CR11871A (ja) |
CY (1) | CY1120617T1 (ja) |
DK (2) | DK2315756T5 (ja) |
EA (2) | EA022669B1 (ja) |
EC (1) | ECSP11010798A (ja) |
ES (2) | ES2524266T3 (ja) |
HK (2) | HK1157692A1 (ja) |
HR (2) | HRP20141094T1 (ja) |
HU (1) | HUE036813T2 (ja) |
IL (2) | IL210402A (ja) |
LT (1) | LT2824100T (ja) |
ME (1) | ME03065B (ja) |
MX (1) | MX2011000235A (ja) |
MY (3) | MY171866A (ja) |
NO (1) | NO2824100T3 (ja) |
NZ (1) | NZ590268A (ja) |
PE (1) | PE20110308A1 (ja) |
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