KR101749232B1 - 에이즈 치료에 유용한 화합물 - Google Patents
에이즈 치료에 유용한 화합물 Download PDFInfo
- Publication number
- KR101749232B1 KR101749232B1 KR1020137018457A KR20137018457A KR101749232B1 KR 101749232 B1 KR101749232 B1 KR 101749232B1 KR 1020137018457 A KR1020137018457 A KR 1020137018457A KR 20137018457 A KR20137018457 A KR 20137018457A KR 101749232 B1 KR101749232 B1 KR 101749232B1
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- South Korea
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- hydrogen atom
- chloro
- methyl
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 136
- 208000030507 AIDS Diseases 0.000 title claims abstract description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 155
- 150000003839 salts Chemical class 0.000 claims abstract description 39
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 26
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 24
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 7
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims abstract description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 54
- -1 4- (trifluoromethyl) pyridin-2-yl Chemical group 0.000 claims description 38
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 26
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 14
- 229910052731 fluorine Inorganic materials 0.000 claims description 13
- 238000003786 synthesis reaction Methods 0.000 claims description 13
- 230000015572 biosynthetic process Effects 0.000 claims description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
- 125000001153 fluoro group Chemical group F* 0.000 claims description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 230000008569 process Effects 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 8
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
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- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 4
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- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 4
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- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 4
- 125000000586 2-(4-morpholinyl)ethoxy group Chemical group [H]C([H])(O*)C([H])([H])N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims description 3
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 230000005764 inhibitory process Effects 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- LWHIWNYBTZRFEP-UHFFFAOYSA-N 2-[(3-amino-4-methylpyridin-2-yl)amino]-5-(dimethylsulfamoylamino)-3-methylquinoline Chemical compound CC=1C=C2C(NS(=O)(=O)N(C)C)=CC=CC2=NC=1NC1=NC=CC(C)=C1N LWHIWNYBTZRFEP-UHFFFAOYSA-N 0.000 claims description 2
- STCNAZVMTAVEOZ-UHFFFAOYSA-N 2-[(3-amino-4-methylpyridin-2-yl)amino]-8-chloro-5-(dimethylsulfamoylamino)quinoline Chemical compound C=1C=C2C(NS(=O)(=O)N(C)C)=CC=C(Cl)C2=NC=1NC1=NC=CC(C)=C1N STCNAZVMTAVEOZ-UHFFFAOYSA-N 0.000 claims description 2
- CDRBXJDVDCNVCR-UHFFFAOYSA-N 2-[4-[(8-chloroquinolin-2-yl)amino]phenoxy]ethanol Chemical compound C1=CC(OCCO)=CC=C1NC1=CC=C(C=CC=C2Cl)C2=N1 CDRBXJDVDCNVCR-UHFFFAOYSA-N 0.000 claims description 2
- FPXYLXAMMKEESV-UHFFFAOYSA-N 2-n-[8-chloro-5-(2-morpholin-4-ylethoxy)quinolin-2-yl]-4-methylpyridine-2,3-diamine Chemical compound CC1=CC=NC(NC=2N=C3C(Cl)=CC=C(OCCN4CCOCC4)C3=CC=2)=C1N FPXYLXAMMKEESV-UHFFFAOYSA-N 0.000 claims description 2
- RWGBXAQMUBGGKQ-UHFFFAOYSA-N 4-(trifluoromethyl)pyridin-2-amine Chemical compound NC1=CC(C(F)(F)F)=CC=N1 RWGBXAQMUBGGKQ-UHFFFAOYSA-N 0.000 claims description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 2
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- 239000011668 ascorbic acid Substances 0.000 claims description 2
- GTEQYEMPPBFZQT-UHFFFAOYSA-N n-[3-methyl-2-[[4-(trifluoromethyl)pyridin-2-yl]amino]quinolin-5-yl]methanesulfonamide Chemical compound CC1=CC2=C(NS(C)(=O)=O)C=CC=C2N=C1NC1=CC(C(F)(F)F)=CC=N1 GTEQYEMPPBFZQT-UHFFFAOYSA-N 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
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- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims 1
- HAVWZAULCLKNBA-UHFFFAOYSA-N n-[2-[3-chloro-4-(trifluoromethoxy)anilino]-3-methylquinolin-5-yl]methanesulfonamide Chemical compound CC1=CC2=C(NS(C)(=O)=O)C=CC=C2N=C1NC1=CC=C(OC(F)(F)F)C(Cl)=C1 HAVWZAULCLKNBA-UHFFFAOYSA-N 0.000 claims 1
- 229910052709 silver Inorganic materials 0.000 claims 1
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- 230000002401 inhibitory effect Effects 0.000 abstract description 7
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- 229940079593 drug Drugs 0.000 abstract description 5
- 125000003545 alkoxy group Chemical group 0.000 abstract description 4
- 125000004428 fluoroalkoxy group Chemical group 0.000 abstract description 3
- 125000003709 fluoroalkyl group Chemical group 0.000 abstract description 3
- 125000005843 halogen group Chemical group 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 75
- 239000011541 reaction mixture Substances 0.000 description 43
- 238000005481 NMR spectroscopy Methods 0.000 description 42
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
- 239000012074 organic phase Substances 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- 238000004440 column chromatography Methods 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- 239000000741 silica gel Substances 0.000 description 15
- 229910002027 silica gel Inorganic materials 0.000 description 15
- 210000004027 cell Anatomy 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 108090000623 proteins and genes Proteins 0.000 description 11
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 10
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- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 8
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- 108020004414 DNA Proteins 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
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- UWZBOFHBRKLFLJ-UHFFFAOYSA-N 4-[2-(4-chloro-3-nitrophenoxy)ethyl]piperidine Chemical compound C1=C(Cl)C([N+](=O)[O-])=CC(OCCC2CCNCC2)=C1 UWZBOFHBRKLFLJ-UHFFFAOYSA-N 0.000 description 4
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- FEWJPZIEWOKRBE-JCYAYHJZSA-L L-tartrate(2-) Chemical compound [O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-L 0.000 description 4
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- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 201000002510 thyroid cancer Diseases 0.000 description 1
- GKYPJLUHGAJKEM-UHFFFAOYSA-N tin;dihydrate Chemical compound O.O.[Sn] GKYPJLUHGAJKEM-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000013519 translation Methods 0.000 description 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 1
- 201000005112 urinary bladder cancer Diseases 0.000 description 1
- 206010046766 uterine cancer Diseases 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- 239000007762 w/o emulsion Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- A61K31/495—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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- A61K31/535—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
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/04—Drugs for disorders of the muscular or neuromuscular system for myasthenia gravis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/12—Ophthalmic agents for cataracts
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/135—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Physical Education & Sports Medicine (AREA)
- Diabetes (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Ophthalmology & Optometry (AREA)
- Virology (AREA)
- Epidemiology (AREA)
- Rheumatology (AREA)
- AIDS & HIV (AREA)
- Neurology (AREA)
- Heart & Thoracic Surgery (AREA)
- Tropical Medicine & Parasitology (AREA)
- Molecular Biology (AREA)
- Hematology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Cardiology (AREA)
- Obesity (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Endocrinology (AREA)
- Dermatology (AREA)
- Emergency Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP10306417.6 | 2010-12-15 | ||
| EP10306417A EP2465502A1 (en) | 2010-12-15 | 2010-12-15 | Compounds useful for treating AIDS |
| PCT/IB2011/055643 WO2012080953A1 (en) | 2010-12-15 | 2011-12-13 | Compounds useful for treating aids |
Publications (2)
| Publication Number | Publication Date |
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| KR20140041402A KR20140041402A (ko) | 2014-04-04 |
| KR101749232B1 true KR101749232B1 (ko) | 2017-07-03 |
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| EP (2) | EP2465502A1 (enExample) |
| JP (1) | JP6049630B2 (enExample) |
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| AU (1) | AU2011342826B2 (enExample) |
| BR (1) | BR112013014943B1 (enExample) |
| CA (1) | CA2819317C (enExample) |
| CU (1) | CU20130080A7 (enExample) |
| DK (1) | DK2651416T3 (enExample) |
| ES (1) | ES2681539T3 (enExample) |
| HR (1) | HRP20181190T1 (enExample) |
| MX (1) | MX337258B (enExample) |
| PL (1) | PL2651416T3 (enExample) |
| PT (1) | PT2651416T (enExample) |
| RU (1) | RU2598845C2 (enExample) |
| WO (1) | WO2012080953A1 (enExample) |
| ZA (1) | ZA201303922B (enExample) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2010143169A2 (en) | 2009-06-12 | 2010-12-16 | Société Splicos | Compounds useful for treating aids |
| US10253020B2 (en) | 2009-06-12 | 2019-04-09 | Abivax | Compounds for preventing, inhibiting, or treating cancer, AIDS and/or premature aging |
| EP2757161A1 (en) | 2013-01-17 | 2014-07-23 | Splicos | miRNA-124 as a biomarker of viral infection |
| MX382692B (es) * | 2013-07-05 | 2025-03-13 | Abivax | Compuestos bicíclicos útiles para el tratamiento de enfermedades causadas por retrovirus. |
| EP2974729A1 (en) | 2014-07-17 | 2016-01-20 | Abivax | Quinoline derivatives for use in the treatment of inflammatory diseases |
| EP2975034A1 (en) * | 2014-07-17 | 2016-01-20 | Abivax | A quinoline derivative for the treatment of inflammatory diseases and AIDS |
| EP3059236A1 (en) | 2015-02-23 | 2016-08-24 | Abivax | A new quinoline derivative for use in the treatment and prevention of viral infections |
| EP3059591A1 (en) * | 2015-02-23 | 2016-08-24 | Abivax | Methods for screening compounds for treating or preventing a viral infection or a virus-related condition |
| EP3058940A1 (en) * | 2015-02-23 | 2016-08-24 | Abivax | Quinoline derivatives for use in the treatment or prevention of viral infection |
| WO2017034986A1 (en) | 2015-08-21 | 2017-03-02 | University Of Kansas | Human tlr8-selective agonists |
| ES2899926T3 (es) | 2016-03-18 | 2022-03-15 | Prosynergia S A R L | Procedimiento para preparar derivados de quinolin-2-il-fenilamina y sus sales |
| KR101966351B1 (ko) * | 2016-06-08 | 2019-04-08 | 한국과학기술연구원 | 히스톤 메틸전달효소 저해용 퀴놀린 유도체 및 이의 용도 |
| WO2019002228A1 (en) | 2017-06-26 | 2019-01-03 | Institut Pasteur | TREATMENTS TO REMOVE HIV RESERVOIRS AND REDUCE VIRAL LOAD |
| WO2019186277A1 (en) | 2018-03-28 | 2019-10-03 | Institut Pasteur | Ultrasensitive hiv-1 p24 detection assay |
| EP3594206A1 (en) | 2018-07-09 | 2020-01-15 | Abivax | Phenyl-n-quinoline derivatives for treating a rna virus infection |
| EP3594205A1 (en) | 2018-07-09 | 2020-01-15 | Abivax | Phenyl-n-aryl derivatives for treating a rna virus infection |
| EP3669873A1 (en) | 2018-12-20 | 2020-06-24 | Abivax | Quinoline derivatives for use ine the traeatment of inflammation diseases |
| WO2020128033A1 (en) | 2018-12-20 | 2020-06-25 | Institut Pasteur | Cellular metabolism of hiv-1 reservoir seeding in cd4+ t cells |
| EP3669874A1 (en) * | 2018-12-20 | 2020-06-24 | Abivax | Quinoline derivatives for use in the treatment or prevention of cancer |
| CN109776498B (zh) * | 2019-03-13 | 2020-04-07 | 浙江永宁药业股份有限公司 | 一种西洛他唑的制备方法 |
| EP4063351A1 (en) * | 2021-03-26 | 2022-09-28 | Abivax | Preparation method of quinoline derivative compounds |
| EP4212156A1 (en) | 2022-01-13 | 2023-07-19 | Abivax | Combination of 8-chloro-n-(4-(trifluoromethoxy)phenyl)quinolin-2-amine and its derivatives with a s1p receptor modulator |
| EP4215196A1 (en) | 2022-01-24 | 2023-07-26 | Abivax | Combination of 8-chloro-n-(4-(trifluoromethoxy)phenyl)quinolin-2-amine and its derivatives with a jak inhibitor |
| TW202436296A (zh) * | 2022-11-25 | 2024-09-16 | 大陸商江蘇恒瑞醫藥股份有限公司 | 喹啉胺類化合物晶型及其製備方法 |
| WO2025027388A1 (en) | 2023-08-01 | 2025-02-06 | Abivax | Obefazimod for treatment of ulcerative colitis |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2419199A (en) * | 1945-02-09 | 1947-04-22 | Parke Davis & Co | Quinoline compounds and process of making same |
| WO1984000489A1 (en) * | 1982-07-26 | 1984-02-16 | American Hospital Supply Corp | Heteroaryl substituted aminomethyl benzene derivatives, compositions and use |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2387229A1 (fr) | 1977-04-13 | 1978-11-10 | Anvar | Dipyrido (4,3-b) (3,4-f) indoles, procede d'obtention, application therapeutique et compositions pharmaceutiques les contenant |
| FR2436786A1 (fr) | 1978-09-21 | 1980-04-18 | Anvar | Nouveaux derives des pyrido (4,3-b) carbazoles (ellipticines), substitues en position 1 par une chaine polyaminee, leur obtention et leur application a titre de medicaments |
| JPS59501318A (ja) * | 1982-07-26 | 1984-07-26 | アメリカン ホスピタル サプライ コ−ポレ−シヨン | ヘテロアリ−ル置換アミノメチルベンゼン誘導体 |
| FR2627493B1 (fr) | 1988-02-23 | 1991-10-31 | Sanofi Sa | Procede de preparation de derives d'isoquinoleine |
| FR2645861A1 (fr) | 1989-04-17 | 1990-10-19 | Inst Nat Sante Rech Med | Utilisation de dipyrido (4,3-b) (3,4-f) indoles pour la preparation de medicaments utiles pour le traitement du sida |
| ATE260099T1 (de) | 1999-04-05 | 2004-03-15 | Hope City | Neue hemmern von fortgeschrittenen glykosilierung-endprodukten |
| UA75055C2 (uk) * | 1999-11-30 | 2006-03-15 | Пфайзер Продактс Інк. | Похідні бензоімідазолу, що використовуються як антипроліферативний засіб, фармацевтична композиція на їх основі |
| EP1542692B1 (en) | 2002-05-22 | 2011-01-05 | Amgen Inc. | Aminopyrimidine derivatives for use as vanilloid receptor ligands for the treatment of pain |
| AU2002950217A0 (en) | 2002-07-16 | 2002-09-12 | Prana Biotechnology Limited | 8- Hydroxy Quinoline Derivatives |
| RU2368604C2 (ru) | 2002-07-19 | 2009-09-27 | Мемори Фармасьютиклз Корпорейшн | Ингибиторы фосфодиэстеразы 4, включающие n-замещенные аналоги анилина и дифениламина |
| FR2849474B3 (fr) | 2002-12-27 | 2004-12-03 | Olivier Jean Noel Juin | Installation de transformation de l'energie cinetique d'un fluide en energie electrique |
| WO2004078731A1 (en) * | 2003-03-06 | 2004-09-16 | 'chemical Diversity Research Institute', Ltd. | Quinoline-carboxylic acids and the derivatives thereof, a focused library |
| FR2859475A1 (fr) | 2003-09-04 | 2005-03-11 | Centre Nat Rech Scient | Utilisation de composes derives d'ellipticine et d'aza-ellipticine pour la preparation d'un medicament utile pour le traitement de maladies genetiques resultant de l'alteration des processus d'epissage |
| FR2859474B1 (fr) | 2003-09-04 | 2006-01-13 | Centre Nat Rech Scient | Utilisation de composes derives d'indole pour la preparation d'un medicament utile pour le traitement de maladies genetiques resultant de l'alteration des processus d'epissage |
| EP1853265B1 (en) | 2005-01-28 | 2016-01-27 | The Government of the United States of America as represented by the Secretary of the Department of Health and Human Services | Farnesyltransferase inhibitors for use in the treatment of laminopathies, cellular aging and atherosclerosis |
| FR2903312B1 (fr) | 2006-07-05 | 2008-09-26 | Univ Aix Marseille Ii | Utilisation d'inhibiteurs d'hmg-coa reductase et de farnesyl-pyrophosphate synthase dans la preparation d'un medicament |
| WO2008008234A1 (en) | 2006-07-07 | 2008-01-17 | Targegen, Inc. | 2-amino-5-substituted pyrimidine inhibitors |
| FR2912745A1 (fr) | 2007-02-19 | 2008-08-22 | Centre Nat Rech Scient | Nouveaux composes derives d'indole et compositions pharmaceutiques les contenant |
| CA2681481A1 (en) | 2007-03-16 | 2008-09-25 | Mount Sinai School Of Medicine | Induction and/or maintenance of tumor dormancy by disruption of urokinase plasminogen activator receptor-integrin interaction |
| CN101679150B (zh) | 2007-05-17 | 2013-05-15 | Lg化学株式会社 | 蒽衍生物和使用该蒽衍生物的有机电子器件 |
| WO2009023844A2 (en) | 2007-08-15 | 2009-02-19 | Memory Pharmaceuticals Corporation | 3' substituted compounds having 5-ht6 receptor affinity |
| FR2926297B1 (fr) | 2008-01-10 | 2013-03-08 | Centre Nat Rech Scient | Molecules chimiques inhibitrices du mecanisme d'epissage pour traiter des maladies resultant d'anomalies d'epissage. |
| WO2010143169A2 (en) * | 2009-06-12 | 2010-12-16 | Société Splicos | Compounds useful for treating aids |
-
2010
- 2010-12-15 EP EP10306417A patent/EP2465502A1/en not_active Withdrawn
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2011
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- 2011-12-13 CA CA2819317A patent/CA2819317C/en active Active
- 2011-12-13 CN CN201180060026.XA patent/CN103415290B/zh active Active
- 2011-12-13 MX MX2013006322A patent/MX337258B/es active IP Right Grant
- 2011-12-13 HR HRP20181190TT patent/HRP20181190T1/hr unknown
- 2011-12-13 EP EP11805230.7A patent/EP2651416B1/en active Active
- 2011-12-13 KR KR1020137018457A patent/KR101749232B1/ko active Active
- 2011-12-13 BR BR112013014943-4A patent/BR112013014943B1/pt active IP Right Grant
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- 2011-12-13 AU AU2011342826A patent/AU2011342826B2/en active Active
- 2011-12-13 PT PT118052307T patent/PT2651416T/pt unknown
- 2011-12-13 WO PCT/IB2011/055643 patent/WO2012080953A1/en not_active Ceased
- 2011-12-13 PL PL11805230T patent/PL2651416T3/pl unknown
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- 2011-12-14 AR ARP110104670A patent/AR084277A1/es active IP Right Grant
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2013
- 2013-05-29 ZA ZA2013/03922A patent/ZA201303922B/en unknown
- 2013-06-13 CU CUP2013000080A patent/CU20130080A7/es unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2419199A (en) * | 1945-02-09 | 1947-04-22 | Parke Davis & Co | Quinoline compounds and process of making same |
| WO1984000489A1 (en) * | 1982-07-26 | 1984-02-16 | American Hospital Supply Corp | Heteroaryl substituted aminomethyl benzene derivatives, compositions and use |
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| Burckhalter, J. H. 외 1명. A new type of 8-quinolinol amebicidal agent. Journal of the American Chemical Society. Vol. 73, 1951년, pp. 4837-4839* |
Also Published As
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| BR112013014943A2 (pt) | 2016-09-13 |
| AU2011342826B2 (en) | 2016-02-11 |
| CA2819317A1 (en) | 2012-06-21 |
| MX337258B (es) | 2016-02-22 |
| CU20130080A7 (es) | 2013-08-29 |
| EP2651416B1 (en) | 2018-05-09 |
| CA2819317C (en) | 2017-02-28 |
| AU2011342826A1 (en) | 2013-07-04 |
| BR112013014943A8 (pt) | 2018-06-12 |
| RU2013126947A (ru) | 2015-01-20 |
| EP2465502A1 (en) | 2012-06-20 |
| CN103415290B (zh) | 2016-09-14 |
| CN103415290A (zh) | 2013-11-27 |
| JP2013545798A (ja) | 2013-12-26 |
| BR112013014943B1 (pt) | 2022-05-03 |
| MX2013006322A (es) | 2013-10-25 |
| DK2651416T3 (en) | 2018-08-06 |
| PT2651416T (pt) | 2018-07-30 |
| PL2651416T3 (pl) | 2018-09-28 |
| JP6049630B2 (ja) | 2016-12-21 |
| AR084277A1 (es) | 2013-05-02 |
| ZA201303922B (en) | 2014-07-30 |
| US9061999B2 (en) | 2015-06-23 |
| EP2651416A1 (en) | 2013-10-23 |
| HRP20181190T1 (hr) | 2019-03-08 |
| KR20140041402A (ko) | 2014-04-04 |
| US20130267703A1 (en) | 2013-10-10 |
| RU2598845C2 (ru) | 2016-09-27 |
| WO2012080953A1 (en) | 2012-06-21 |
| ES2681539T3 (es) | 2018-09-13 |
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