SI2824100T1 - 1,2,5-oxadiazoles as inhibitors of indolamine 2,3-dioxygenase - Google Patents
1,2,5-oxadiazoles as inhibitors of indolamine 2,3-dioxygenase Download PDFInfo
- Publication number
- SI2824100T1 SI2824100T1 SI200931815T SI200931815T SI2824100T1 SI 2824100 T1 SI2824100 T1 SI 2824100T1 SI 200931815 T SI200931815 T SI 200931815T SI 200931815 T SI200931815 T SI 200931815T SI 2824100 T1 SI2824100 T1 SI 2824100T1
- Authority
- SI
- Slovenia
- Prior art keywords
- amino
- oxadiazole
- cancer
- carboximidamide
- hydroxy
- Prior art date
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- 150000002244 furazanes Chemical class 0.000 title claims abstract 4
- 239000003112 inhibitor Substances 0.000 title claims abstract 3
- 102000006639 indoleamine 2,3-dioxygenase Human genes 0.000 title abstract 2
- 108020004201 indoleamine 2,3-dioxygenase Proteins 0.000 title abstract 2
- 206010028980 Neoplasm Diseases 0.000 claims abstract 12
- 201000011510 cancer Diseases 0.000 claims abstract 12
- 150000003839 salts Chemical class 0.000 claims 19
- 150000001875 compounds Chemical class 0.000 claims 18
- 239000007787 solid Substances 0.000 claims 10
- -1 N- (3-chloro-4-fluorophenyl) hydroxy-4 - ({2 - [(methylsulfonyl) amino] ethyl} amino) -1,2,5-oxadiazole-3-carboximidamide Chemical compound 0.000 claims 7
- 238000000634 powder X-ray diffraction Methods 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- 206010006187 Breast cancer Diseases 0.000 claims 2
- 208000026310 Breast neoplasm Diseases 0.000 claims 2
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 2
- FBKMWOJEPMPVTQ-UHFFFAOYSA-N N'-(3-bromo-4-fluorophenyl)-N-hydroxy-4-[2-(sulfamoylamino)ethylamino]-1,2,5-oxadiazole-3-carboximidamide Chemical compound NS(=O)(=O)NCCNC1=NON=C1C(=NO)NC1=CC=C(F)C(Br)=C1 FBKMWOJEPMPVTQ-UHFFFAOYSA-N 0.000 claims 2
- 206010033128 Ovarian cancer Diseases 0.000 claims 2
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 2
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 2
- 206010060862 Prostate cancer Diseases 0.000 claims 2
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 2
- 201000005202 lung cancer Diseases 0.000 claims 2
- 208000020816 lung neoplasm Diseases 0.000 claims 2
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 2
- 201000001441 melanoma Diseases 0.000 claims 2
- 201000002528 pancreatic cancer Diseases 0.000 claims 2
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- TXQAZWIBPGKHOX-UHFFFAOYSA-N 1H-indol-3-amine Chemical compound C1=CC=C2C(N)=CNC2=C1 TXQAZWIBPGKHOX-UHFFFAOYSA-N 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- 208000003174 Brain Neoplasms Diseases 0.000 claims 1
- 206010008342 Cervix carcinoma Diseases 0.000 claims 1
- 208000005016 Intestinal Neoplasms Diseases 0.000 claims 1
- 208000008839 Kidney Neoplasms Diseases 0.000 claims 1
- 206010025323 Lymphomas Diseases 0.000 claims 1
- UCDYISCEVMDSNZ-UHFFFAOYSA-N N'-(3-bromo-4-fluorophenyl)-N-hydroxy-4-[2-(methanesulfonamido)ethylamino]-1,2,5-oxadiazole-3-carboximidamide Chemical compound CS(=O)(=O)NCCNC1=NON=C1C(=NO)NC1=CC=C(F)C(Br)=C1 UCDYISCEVMDSNZ-UHFFFAOYSA-N 0.000 claims 1
- AKAHHYVXFPVMIG-UHFFFAOYSA-N N'-(3-bromo-4-fluorophenyl)-N-hydroxy-4-[3-(methanesulfonamido)propylamino]-1,2,5-oxadiazole-3-carboximidamide Chemical compound CS(=O)(=O)NCCCNC1=NON=C1C(=NO)NC1=CC=C(F)C(Br)=C1 AKAHHYVXFPVMIG-UHFFFAOYSA-N 0.000 claims 1
- WZVAULHJNFGOBR-UHFFFAOYSA-N N'-(3-chloro-4-fluorophenyl)-N-hydroxy-4-[2-(sulfamoylamino)ethylamino]-1,2,5-oxadiazole-3-carboximidamide Chemical compound NS(=O)(=O)NCCNC1=NON=C1C(=NO)NC1=CC=C(F)C(Cl)=C1 WZVAULHJNFGOBR-UHFFFAOYSA-N 0.000 claims 1
- GHLDPOHYOPWBDC-UHFFFAOYSA-N N'-(3-cyano-4-fluorophenyl)-N-hydroxy-4-[2-(methanesulfonamido)ethylamino]-1,2,5-oxadiazole-3-carboximidamide Chemical compound CS(=O)(=O)NCCNC1=NON=C1C(=NO)NC1=CC=C(F)C(C#N)=C1 GHLDPOHYOPWBDC-UHFFFAOYSA-N 0.000 claims 1
- UCXWHYTXLXWOJD-UHFFFAOYSA-N N'-(4-fluoro-3-methylphenyl)-N-hydroxy-4-[2-(methanesulfonamido)ethylamino]-1,2,5-oxadiazole-3-carboximidamide Chemical compound C1=C(F)C(C)=CC(NC(=NO)C=2C(=NON=2)NCCNS(C)(=O)=O)=C1 UCXWHYTXLXWOJD-UHFFFAOYSA-N 0.000 claims 1
- OGQZJUFNXXNGST-UHFFFAOYSA-N N'-[(4-bromofuran-2-yl)methyl]-N-hydroxy-4-[2-(sulfamoylamino)ethylamino]-1,2,5-oxadiazole-3-carboximidamide Chemical compound NS(=O)(=O)NCCNC1=NON=C1C(=NO)NCC1=CC(Br)=CO1 OGQZJUFNXXNGST-UHFFFAOYSA-N 0.000 claims 1
- RDUXAXXIUDRDCQ-UHFFFAOYSA-N N'-[(4-chlorofuran-2-yl)methyl]-N-hydroxy-4-[2-(sulfamoylamino)ethylamino]-1,2,5-oxadiazole-3-carboximidamide Chemical compound NS(=O)(=O)NCCNC1=NON=C1C(=NO)NCC1=CC(Cl)=CO1 RDUXAXXIUDRDCQ-UHFFFAOYSA-N 0.000 claims 1
- JIVHKHGOKPSNGR-UHFFFAOYSA-N N'-[4-fluoro-3-(trifluoromethyl)phenyl]-N-hydroxy-4-[2-(sulfamoylamino)ethylamino]-1,2,5-oxadiazole-3-carboximidamide 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
- YHEQSGUVCLJBDT-UHFFFAOYSA-N N'-[4-fluoro-3-(trifluoromethyl)phenyl]-N-hydroxy-4-[3-(methanesulfonamido)propylamino]-1,2,5-oxadiazole-3-carboximidamide 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
- HMNCIHXNFCSJKK-UHFFFAOYSA-N N'-[4-fluoro-3-(trifluoromethyl)phenyl]-N-hydroxy-4-[3-(sulfamoylamino)propylamino]-1,2,5-oxadiazole-3-carboximidamide 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
- OXNMGSAIPOICQS-UHFFFAOYSA-N N'-hydroxy-4-[2-(methanesulfonamido)ethylamino]-1,2,5-oxadiazole-3-carboximidamide Chemical compound CS(=O)(=O)NCCNC1=NON=C1C(N)=NO OXNMGSAIPOICQS-UHFFFAOYSA-N 0.000 claims 1
- VFEHBKRICPOHDX-UHFFFAOYSA-N N-hydroxy-4-[2-(methanesulfonamido)ethylamino]-N'-[3-(trifluoromethyl)phenyl]-1,2,5-oxadiazole-3-carboximidamide Chemical compound CS(=O)(=O)NCCNC1=NON=C1C(=NO)NC1=CC=CC(C(F)(F)F)=C1 VFEHBKRICPOHDX-UHFFFAOYSA-N 0.000 claims 1
- XWCIZKDALWTABF-UHFFFAOYSA-N N-hydroxy-4-[2-(sulfamoylamino)ethylamino]-N'-[3-(trifluoromethyl)phenyl]-1,2,5-oxadiazole-3-carboximidamide Chemical compound NS(=O)(=O)NCCNC1=NON=C1C(=NO)NC1=CC=CC(C(F)(F)F)=C1 XWCIZKDALWTABF-UHFFFAOYSA-N 0.000 claims 1
- NQNWGOYDURQABD-UHFFFAOYSA-N N-hydroxy-4-[3-(methanesulfonamido)propylamino]-N'-[3-(trifluoromethyl)phenyl]-1,2,5-oxadiazole-3-carboximidamide Chemical compound CS(=O)(=O)NCCCNC1=NON=C1C(=NO)NC1=CC=CC(C(F)(F)F)=C1 NQNWGOYDURQABD-UHFFFAOYSA-N 0.000 claims 1
- ASBHTDHDYPGYMC-UHFFFAOYSA-N N-hydroxy-4-[3-(sulfamoylamino)propylamino]-N'-[3-(trifluoromethyl)phenyl]-1,2,5-oxadiazole-3-carboximidamide Chemical compound NS(=O)(=O)NCCCNC1=NON=C1C(=NO)NC1=CC=CC(C(F)(F)F)=C1 ASBHTDHDYPGYMC-UHFFFAOYSA-N 0.000 claims 1
- 206010038389 Renal cancer Diseases 0.000 claims 1
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 1
- 201000010881 cervical cancer Diseases 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 201000010536 head and neck cancer Diseases 0.000 claims 1
- 208000014829 head and neck neoplasm Diseases 0.000 claims 1
- 201000002313 intestinal cancer Diseases 0.000 claims 1
- 201000010982 kidney cancer Diseases 0.000 claims 1
- 208000032839 leukemia Diseases 0.000 claims 1
- 230000008018 melting Effects 0.000 claims 1
- 238000002844 melting Methods 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- 210000001550 testis Anatomy 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
Classifications
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4245—Oxadiazoles
-
- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- A61K39/39533—Antibodies; Immunoglobulins; Immune serum, e.g. antilymphocytic serum against materials from animals
- A61K39/3955—Antibodies; Immunoglobulins; Immune serum, e.g. antilymphocytic serum against materials from animals against proteinaceous materials, e.g. enzymes, hormones, lymphokines
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/08—1,2,5-Oxadiazoles; Hydrogenated 1,2,5-oxadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Epidemiology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Oncology (AREA)
- Virology (AREA)
- Communicable Diseases (AREA)
- Psychiatry (AREA)
- Ophthalmology & Optometry (AREA)
- Dermatology (AREA)
- Pain & Pain Management (AREA)
- Microbiology (AREA)
- Mycology (AREA)
- Endocrinology (AREA)
- AIDS & HIV (AREA)
- Hospice & Palliative Care (AREA)
- Pulmonology (AREA)
- Physical Education & Sports Medicine (AREA)
- Molecular Biology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Rheumatology (AREA)
- Hematology (AREA)
- Transplantation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US7887608P | 2008-07-08 | 2008-07-08 | |
| US15087309P | 2009-02-09 | 2009-02-09 | |
| EP14175271.7A EP2824100B1 (en) | 2008-07-08 | 2009-07-07 | 1,2,5-Oxadiazoles as inhibitors of indoleamine 2,3-dioxygenase |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SI2824100T1 true SI2824100T1 (en) | 2018-06-29 |
Family
ID=41128289
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SI200931815T SI2824100T1 (en) | 2008-07-08 | 2009-07-07 | 1,2,5-oxadiazoles as inhibitors of indolamine 2,3-dioxygenase |
| SI200931066T SI2315756T1 (sl) | 2008-07-08 | 2009-07-07 | 1,2,5-oksadiazoli kot inhibitorji indolamin 2,3-dioksigenaze |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SI200931066T SI2315756T1 (sl) | 2008-07-08 | 2009-07-07 | 1,2,5-oksadiazoli kot inhibitorji indolamin 2,3-dioksigenaze |
Country Status (36)
| Country | Link |
|---|---|
| US (12) | US8088803B2 (OSRAM) |
| EP (3) | EP2824100B1 (OSRAM) |
| JP (2) | JP5465720B2 (OSRAM) |
| KR (5) | KR101847107B1 (OSRAM) |
| CN (2) | CN104042611B (OSRAM) |
| AR (1) | AR072490A1 (OSRAM) |
| AU (6) | AU2009268739B2 (OSRAM) |
| BR (2) | BRPI0915692B8 (OSRAM) |
| CA (2) | CA2743975C (OSRAM) |
| CL (2) | CL2009001554A1 (OSRAM) |
| CO (1) | CO6341622A2 (OSRAM) |
| CR (1) | CR11871A (OSRAM) |
| CY (1) | CY1120617T1 (OSRAM) |
| DK (2) | DK2824100T3 (OSRAM) |
| EA (2) | EA029781B1 (OSRAM) |
| EC (1) | ECSP11010798A (OSRAM) |
| ES (2) | ES2665419T3 (OSRAM) |
| HR (2) | HRP20141094T1 (OSRAM) |
| HU (1) | HUE036813T2 (OSRAM) |
| IL (2) | IL210402A (OSRAM) |
| LT (1) | LT2824100T (OSRAM) |
| ME (1) | ME03065B (OSRAM) |
| MX (1) | MX2011000235A (OSRAM) |
| MY (3) | MY171866A (OSRAM) |
| NO (1) | NO2824100T3 (OSRAM) |
| NZ (1) | NZ590268A (OSRAM) |
| PE (1) | PE20110308A1 (OSRAM) |
| PH (1) | PH12014500947B1 (OSRAM) |
| PL (2) | PL2315756T3 (OSRAM) |
| PT (2) | PT2824100T (OSRAM) |
| RS (2) | RS53688B9 (OSRAM) |
| SG (2) | SG192485A1 (OSRAM) |
| SI (2) | SI2824100T1 (OSRAM) |
| SM (2) | SMT201800206T1 (OSRAM) |
| TW (1) | TWI453204B (OSRAM) |
| WO (1) | WO2010005958A2 (OSRAM) |
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