JP2000516231A - 免疫調節物質としての４―置換β―カルボリン - Google Patents
免疫調節物質としての４―置換β―カルボリンInfo
- Publication number
- JP2000516231A JP2000516231A JP10509821A JP50982198A JP2000516231A JP 2000516231 A JP2000516231 A JP 2000516231A JP 10509821 A JP10509821 A JP 10509821A JP 50982198 A JP50982198 A JP 50982198A JP 2000516231 A JP2000516231 A JP 2000516231A
- Authority
- JP
- Japan
- Prior art keywords
- branched
- unbranched
- group
- alkyl
- phenyl
- Prior art date
- 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.)
- Ceased
Links
- AIFRHYZBTHREPW-UHFFFAOYSA-N β-carboline Chemical class N1=CC=C2C3=CC=CC=C3NC2=C1 AIFRHYZBTHREPW-UHFFFAOYSA-N 0.000 title abstract description 55
- 239000002955 immunomodulating agent Substances 0.000 title description 2
- 229940121354 immunomodulator Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 84
- 108010002350 Interleukin-2 Proteins 0.000 claims abstract description 20
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- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 12
- 208000026278 immune system disease Diseases 0.000 claims abstract description 8
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- 230000004941 influx Effects 0.000 claims abstract description 6
- 210000000056 organ Anatomy 0.000 claims abstract description 6
- 230000001404 mediated effect Effects 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 58
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 53
- 125000003342 alkenyl group Chemical group 0.000 claims description 39
- -1 NR 3 R 4 Chemical group 0.000 claims description 36
- 125000003545 alkoxy group Chemical group 0.000 claims description 33
- 125000000304 alkynyl group Chemical group 0.000 claims description 33
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 27
- 125000000623 heterocyclic group Chemical group 0.000 claims description 25
- 125000001475 halogen functional group Chemical group 0.000 claims description 23
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 230000015572 biosynthetic process Effects 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 230000004073 interleukin-2 production Effects 0.000 claims description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000002671 adjuvant Substances 0.000 claims description 10
- SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 10
- 125000001624 naphthyl group Chemical group 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 238000003786 synthesis reaction Methods 0.000 claims description 10
- 125000006239 protecting group Chemical group 0.000 claims description 9
- CFTOTSJVQRFXOF-UHFFFAOYSA-N 2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole Chemical class N1C2=CC=CC=C2C2=C1CNCC2 CFTOTSJVQRFXOF-UHFFFAOYSA-N 0.000 claims description 8
- 239000003937 drug carrier Substances 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical group 0.000 claims description 7
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 7
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 125000001544 thienyl group Chemical group 0.000 claims description 7
- 125000002541 furyl group Chemical group 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000000335 thiazolyl group Chemical group 0.000 claims description 6
- APJYDQYYACXCRM-UHFFFAOYSA-N tryptamine Chemical compound C1=CC=C2C(CCN)=CNC2=C1 APJYDQYYACXCRM-UHFFFAOYSA-N 0.000 claims description 6
- GQUKRVSEJIFCKJ-UHFFFAOYSA-N 4-[4-(trifluoromethyl)phenyl]-9h-pyrido[3,4-b]indole Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CN=CC2=C1C1=CC=CC=C1N2 GQUKRVSEJIFCKJ-UHFFFAOYSA-N 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
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- PIAOLBVUVDXHHL-VOTSOKGWSA-N β-nitrostyrene Chemical compound [O-][N+](=O)\C=C\C1=CC=CC=C1 PIAOLBVUVDXHHL-VOTSOKGWSA-N 0.000 claims description 5
- DCBDOYDVQJVXOH-UHFFFAOYSA-N azane;1h-indole Chemical compound N.C1=CC=C2NC=CC2=C1 DCBDOYDVQJVXOH-UHFFFAOYSA-N 0.000 claims description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
- 150000002690 malonic acid derivatives Chemical class 0.000 claims description 4
- 125000006513 pyridinyl methyl group Chemical group 0.000 claims description 4
- NTYXKFHKVREUMR-UHFFFAOYSA-N 4,9-dihydro-3h-pyrido[3,4-b]indole Chemical class N1C2=CC=CC=C2C2=C1C=NCC2 NTYXKFHKVREUMR-UHFFFAOYSA-N 0.000 claims description 3
- LQNGWEGPWIPDPM-UHFFFAOYSA-N 4-(4-methoxyphenyl)-9h-pyrido[3,4-b]indole Chemical compound C1=CC(OC)=CC=C1C1=CN=CC2=C1C1=CC=CC=C1N2 LQNGWEGPWIPDPM-UHFFFAOYSA-N 0.000 claims description 3
- DEPRPCSXNYCOPR-UHFFFAOYSA-N 4-(4-methylphenyl)-9h-pyrido[3,4-b]indole Chemical compound C1=CC(C)=CC=C1C1=CN=CC2=C1C1=CC=CC=C1N2 DEPRPCSXNYCOPR-UHFFFAOYSA-N 0.000 claims description 3
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- 150000001350 alkyl halides Chemical class 0.000 claims description 3
- LTMHNWPUDSTBKD-UHFFFAOYSA-N diethyl 2-(ethoxymethylidene)propanedioate Chemical compound CCOC=C(C(=O)OCC)C(=O)OCC LTMHNWPUDSTBKD-UHFFFAOYSA-N 0.000 claims description 3
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- ZXLDQJLIBNPEFJ-UHFFFAOYSA-N tetrahydro-beta-carboline Natural products C1CNC(C)C2=C1C1=CC=C(OC)C=C1N2 ZXLDQJLIBNPEFJ-UHFFFAOYSA-N 0.000 claims description 3
- 206010009900 Colitis ulcerative Diseases 0.000 claims description 2
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- 206010025135 lupus erythematosus Diseases 0.000 claims description 2
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- 238000002054 transplantation Methods 0.000 claims description 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 7
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- 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
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- 108060003951 Immunoglobulin Proteins 0.000 claims 1
- 102000018358 immunoglobulin Human genes 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- KQTZKCVKUMQTNJ-UHFFFAOYSA-N n,n-dimethyl-4-(9h-pyrido[3,4-b]indol-4-yl)aniline Chemical compound C1=CC(N(C)C)=CC=C1C1=CN=CC2=C1C1=CC=CC=C1N2 KQTZKCVKUMQTNJ-UHFFFAOYSA-N 0.000 claims 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 1
- 238000011282 treatment Methods 0.000 abstract description 11
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 39
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 13
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- 150000003839 salts Chemical class 0.000 description 12
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- 239000011777 magnesium Substances 0.000 description 1
- RYEXTBOQKFUPOE-UHFFFAOYSA-M magnesium;propane;chloride Chemical compound [Mg+2].[Cl-].CC[CH2-] RYEXTBOQKFUPOE-UHFFFAOYSA-M 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000003550 marker Substances 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
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- 239000002609 medium Substances 0.000 description 1
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- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000002911 monocyclic heterocycle group Chemical group 0.000 description 1
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical class C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
- 229960004927 neomycin Drugs 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- LVSJDHGRKAEGLX-UHFFFAOYSA-N oxolane;2,2,2-trifluoroacetic acid Chemical compound C1CCOC1.OC(=O)C(F)(F)F LVSJDHGRKAEGLX-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 230000010412 perfusion Effects 0.000 description 1
- 210000005105 peripheral blood lymphocyte Anatomy 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229960003531 phenolsulfonphthalein Drugs 0.000 description 1
- DHHVAGZRUROJKS-UHFFFAOYSA-N phentermine Chemical compound CC(C)(N)CC1=CC=CC=C1 DHHVAGZRUROJKS-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229940075930 picrate Drugs 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
- 229950010765 pivalate Drugs 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 230000029279 positive regulation of transcription, DNA-dependent Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- NRTYMEPCRDJMPZ-UHFFFAOYSA-N pyridine;2,2,2-trifluoroacetic acid Chemical group C1=CC=NC=C1.OC(=O)C(F)(F)F NRTYMEPCRDJMPZ-UHFFFAOYSA-N 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 238000005956 quaternization reaction Methods 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000003757 reverse transcription PCR Methods 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 238000009097 single-agent therapy Methods 0.000 description 1
- AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000003507 tetrahydrothiofenyl group Chemical group 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000006090 thiamorpholinyl sulfone group Chemical group 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 238000013518 transcription Methods 0.000 description 1
- 230000035897 transcription Effects 0.000 description 1
- 238000011269 treatment regimen Methods 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000004933 β-carbolinyl group Chemical group C1(=NC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Immunology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2365096P | 1996-08-09 | 1996-08-09 | |
| US60/023,650 | 1996-08-09 | ||
| PCT/US1997/013767 WO1998006719A1 (en) | 1996-08-09 | 1997-08-08 | 4-substituted beta-carbolines as immunomodulators |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2000516231A true JP2000516231A (ja) | 2000-12-05 |
| JP2000516231A5 JP2000516231A5 (enExample) | 2005-04-07 |
Family
ID=21816410
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10509821A Ceased JP2000516231A (ja) | 1996-08-09 | 1997-08-08 | 免疫調節物質としての４―置換β―カルボリン |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US6093723A (enExample) |
| EP (1) | EP0923581B1 (enExample) |
| JP (1) | JP2000516231A (enExample) |
| AT (1) | ATE240955T1 (enExample) |
| CA (1) | CA2262796C (enExample) |
| DE (1) | DE69722220T2 (enExample) |
| DK (1) | DK0923581T3 (enExample) |
| ES (1) | ES2194213T3 (enExample) |
| PT (1) | PT923581E (enExample) |
| WO (1) | WO1998006719A1 (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009511503A (ja) * | 2005-10-07 | 2009-03-19 | タケダ サン ディエゴ インコーポレイテッド | キナーゼ阻害剤 |
| WO2010073719A1 (ja) * | 2008-12-26 | 2010-07-01 | 国立大学法人京都大学 | Ｅｇ５阻害剤 |
| JP2010163365A (ja) * | 2009-01-13 | 2010-07-29 | Sakamoto Jozo Kk | 潰瘍性大腸炎治療薬 |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003518494A (ja) * | 1999-12-29 | 2003-06-10 | グラクソ グループ リミテッド | アネキシンおよび軟骨ホメオスタシスのモジュレーターに関係する方法と組成物 |
| EP1134221A1 (en) * | 2000-03-15 | 2001-09-19 | Aventis Pharma Deutschland GmbH | Substituted beta-carbolines as lkB kinase inhibitors |
| CA2402549A1 (en) * | 2000-03-15 | 2001-09-20 | Aventis Pharma Deutschland Gmbh | Substituted beta-carbolines |
| US6379900B1 (en) | 2000-05-09 | 2002-04-30 | Conceptual Mindworks, Inc. | Compositions and methods of use of 8-nitroguanine |
| US20030045541A1 (en) * | 2001-07-23 | 2003-03-06 | Christopher Bruckner | GABA-Receptor modulators with NMDA-Antagonistic activity |
| WO2006115509A2 (en) | 2004-06-24 | 2006-11-02 | Novartis Vaccines And Diagnostics Inc. | Small molecule immunopotentiators and assays for their detection |
| US8703726B2 (en) | 2009-05-27 | 2014-04-22 | Ptc Therapeutics, Inc. | Methods for treating prostate conditions |
| US8697662B2 (en) | 2009-05-27 | 2014-04-15 | Ptc Therapeutics, Inc. | Methods for treating Kaposi sarcoma |
| JP2012528181A (ja) * | 2009-05-27 | 2012-11-12 | ピーティーシー セラピューティクス，インコーポレーテッド | 置換テトラヒドロβ−カルボリンの製造方法 |
| MX373926B (es) | 2009-05-27 | 2020-07-10 | Ptc Therapeutics Inc | Metodos para tratar cancer y estados no neoplasicos. |
| US10703722B2 (en) | 2010-04-27 | 2020-07-07 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| EP2563759B1 (en) | 2010-04-27 | 2022-04-06 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| PT2563776T (pt) | 2010-04-27 | 2016-09-19 | Calcimedica Inc | Compostos que modulam o cálcio intracelular |
| CA2809830C (en) | 2010-08-27 | 2019-09-10 | Calcimedica, Inc. | Compounds comprising n-acyl-2-amino-1,3-thiazole for modulating intracellular calcium |
| KR101840313B1 (ko) * | 2011-02-14 | 2018-03-21 | 에스에프씨 주식회사 | 피리딘 유도체 화합물 및 이를 포함하는 유기전계발광소자 |
| US20120316182A1 (en) | 2011-06-10 | 2012-12-13 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| WO2013059677A1 (en) | 2011-10-19 | 2013-04-25 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| CA2863517C (en) * | 2012-01-20 | 2019-11-05 | Genosco | Substituted pyrimidine compounds and their use as syk inhibitors |
| US9512116B2 (en) | 2012-10-12 | 2016-12-06 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| US10046002B2 (en) | 2013-08-02 | 2018-08-14 | Syntrix Biosystems Inc. | Method for treating cancer using chemokine antagonists |
| US10561676B2 (en) | 2013-08-02 | 2020-02-18 | Syntrix Biosystems Inc. | Method for treating cancer using dual antagonists of CXCR1 and CXCR2 |
| US8969365B2 (en) | 2013-08-02 | 2015-03-03 | Syntrix Biosystems, Inc. | Thiopyrimidinecarboxamides as CXCR1/2 modulators |
| EP3778595B1 (en) | 2015-02-27 | 2021-08-25 | Calcimedica, Inc. | Pancreatitis treatment |
| EP3331525B1 (en) | 2015-08-07 | 2020-10-07 | Calcimedica, Inc. | Use of crac channel inhibitors for the treatment of stroke and traumatic brain injury |
| EP3664803A4 (en) | 2017-08-01 | 2021-05-05 | PTC Therapeutics, Inc. | DHODH INHIBITOR FOR USE IN THE TREATMENT OF HEMATOLOGICAL CANCERS |
| US11117893B2 (en) * | 2018-09-24 | 2021-09-14 | Union University | Methods for preparation of substituted pyridines and related novel compounds |
| US12522589B2 (en) | 2020-11-13 | 2026-01-13 | Calcimedica, Inc. | Synthesis of CRAC channel inhibitors |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ194747A (en) * | 1979-08-29 | 1988-11-29 | Schering Ag | 9h-pyrido(3,4-b)indol-3-ylcarboxylic acid derivatives |
| SU859889A1 (ru) * | 1980-01-17 | 1981-08-30 | Читинский Медицинский Институт | Способ количественного определени 1-метил-4-(N-метилпирролидил-1)- -карболин гидрохлорида |
| DE3240514A1 (de) * | 1982-10-29 | 1984-05-03 | Schering AG, 1000 Berlin und 4709 Bergkamen | Ss-carboline, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate |
| US5359078A (en) * | 1989-05-19 | 1994-10-25 | The United States Of America As Represented By The Department Of Health And Human Services | Signal transduction inhibitor compounds |
| WO1991013627A1 (en) * | 1990-03-14 | 1991-09-19 | The Board Of Regents, The University Of Texas System | Tripterygium wilfordii hook f extracts and components thereof for immunosuppression |
| DK0610744T3 (da) * | 1993-02-09 | 1999-07-19 | Bayer Ag | Sulfonamidaminomethylenderivater som immunosuppressive stoffer |
| JPH07112918A (ja) * | 1993-10-15 | 1995-05-02 | Pola Chem Ind Inc | 育毛剤及びこれを含有する頭髪用化粧料 |
| DE19502753A1 (de) * | 1995-01-23 | 1996-07-25 | Schering Ag | Neue 9H-Pyrido[3,4-b]indol-Derivate |
-
1997
- 1997-08-08 DE DE69722220T patent/DE69722220T2/de not_active Expired - Fee Related
- 1997-08-08 ES ES97938122T patent/ES2194213T3/es not_active Expired - Lifetime
- 1997-08-08 AT AT97938122T patent/ATE240955T1/de not_active IP Right Cessation
- 1997-08-08 PT PT97938122T patent/PT923581E/pt unknown
- 1997-08-08 CA CA002262796A patent/CA2262796C/en not_active Expired - Fee Related
- 1997-08-08 EP EP97938122A patent/EP0923581B1/en not_active Expired - Lifetime
- 1997-08-08 US US08/908,211 patent/US6093723A/en not_active Expired - Lifetime
- 1997-08-08 WO PCT/US1997/013767 patent/WO1998006719A1/en not_active Ceased
- 1997-08-08 JP JP10509821A patent/JP2000516231A/ja not_active Ceased
- 1997-08-08 DK DK97938122T patent/DK0923581T3/da active
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009511503A (ja) * | 2005-10-07 | 2009-03-19 | タケダ サン ディエゴ インコーポレイテッド | キナーゼ阻害剤 |
| WO2010073719A1 (ja) * | 2008-12-26 | 2010-07-01 | 国立大学法人京都大学 | Ｅｇ５阻害剤 |
| JP2010163365A (ja) * | 2009-01-13 | 2010-07-29 | Sakamoto Jozo Kk | 潰瘍性大腸炎治療薬 |
Also Published As
| Publication number | Publication date |
|---|---|
| ATE240955T1 (de) | 2003-06-15 |
| EP0923581B1 (en) | 2003-05-21 |
| US6093723A (en) | 2000-07-25 |
| DE69722220D1 (de) | 2003-06-26 |
| WO1998006719A1 (en) | 1998-02-19 |
| CA2262796A1 (en) | 1998-02-19 |
| DE69722220T2 (de) | 2004-02-19 |
| CA2262796C (en) | 2006-10-31 |
| DK0923581T3 (da) | 2003-08-04 |
| PT923581E (pt) | 2003-10-31 |
| ES2194213T3 (es) | 2003-11-16 |
| EP0923581A1 (en) | 1999-06-23 |
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