KR102575601B1 - 치환된 트리아졸 및 이와 관련된 방법 - Google Patents
치환된 트리아졸 및 이와 관련된 방법 Download PDFInfo
- Publication number
- KR102575601B1 KR102575601B1 KR1020177023771A KR20177023771A KR102575601B1 KR 102575601 B1 KR102575601 B1 KR 102575601B1 KR 1020177023771 A KR1020177023771 A KR 1020177023771A KR 20177023771 A KR20177023771 A KR 20177023771A KR 102575601 B1 KR102575601 B1 KR 102575601B1
- Authority
- KR
- South Korea
- Prior art keywords
- methyl
- triazol
- alkyl
- compound
- difluorophenyl
- 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.)
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- 238000000034 method Methods 0.000 title claims abstract description 114
- 150000003852 triazoles Chemical class 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 176
- 238000011282 treatment Methods 0.000 claims abstract description 36
- 150000003839 salts Chemical class 0.000 claims abstract description 28
- 239000012453 solvate Substances 0.000 claims abstract description 17
- 239000003937 drug carrier Substances 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 69
- -1 2,6-difluorophenyl Chemical group 0.000 claims description 38
- 125000000623 heterocyclic group Chemical group 0.000 claims description 28
- 201000006517 essential tremor Diseases 0.000 claims description 24
- 206010015037 epilepsy Diseases 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- 239000003795 chemical substances by application Substances 0.000 claims description 16
- 229910052799 carbon Inorganic materials 0.000 claims description 15
- 239000008194 pharmaceutical composition Substances 0.000 claims description 15
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 12
- 210000005036 nerve Anatomy 0.000 claims description 12
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 7
- 239000003085 diluting agent Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 125000001041 indolyl group Chemical group 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- BDDGNXKWJXXPMI-UHFFFAOYSA-N 1-[(2,6-difluorophenyl)methyl]-N,N-dimethyltriazol-4-amine Chemical compound FC1=C(CN2N=NC(=C2)N(C)C)C(=CC=C1)F BDDGNXKWJXXPMI-UHFFFAOYSA-N 0.000 claims description 6
- WRWGTYNZFVAKNT-UHFFFAOYSA-N 1-[(2,6-difluorophenyl)methyl]-n-methyltriazol-4-amine Chemical compound N1=NC(NC)=CN1CC1=C(F)C=CC=C1F WRWGTYNZFVAKNT-UHFFFAOYSA-N 0.000 claims description 6
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- 125000002883 imidazolyl group Chemical group 0.000 claims description 6
- ZUASMCSOQJBASC-UHFFFAOYSA-N 1-[1-[(2,6-difluorophenyl)methyl]triazol-4-yl]imidazolidin-2-one Chemical compound FC1=C(C(=CC=C1)F)CN1N=NC(=C1)N1C(NCC1)=O ZUASMCSOQJBASC-UHFFFAOYSA-N 0.000 claims description 5
- NNOBBZLWKCXSBK-UHFFFAOYSA-N 2-[[1-[(2,6-difluorophenyl)methyl]triazol-4-yl]amino]ethanol Chemical compound FC1=C(C(=CC=C1)F)CN1N=NC(=C1)NCCO NNOBBZLWKCXSBK-UHFFFAOYSA-N 0.000 claims description 5
- ZKGWDRDIXBWEBX-UHFFFAOYSA-N 4-[1-[(2,6-difluorophenyl)methyl]triazol-4-yl]morpholine Chemical compound FC1=C(C(=CC=C1)F)CN1N=NC(=C1)N1CCOCC1 ZKGWDRDIXBWEBX-UHFFFAOYSA-N 0.000 claims description 5
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 5
- RVIIAZDTPXSBSA-INIZCTEOSA-N (2S)-2-amino-N-[1-[(2,6-difluorophenyl)methyl]triazol-4-yl]-3-phenylpropanamide Chemical compound N[C@H](C(=O)NC=1N=NN(C=1)CC1=C(C=CC=C1F)F)CC1=CC=CC=C1 RVIIAZDTPXSBSA-INIZCTEOSA-N 0.000 claims description 4
- CPMYTQMQHAYCBW-UHFFFAOYSA-N 1-[(2,6-difluorophenyl)methyl]-4-pyrrolidin-1-yltriazole Chemical compound FC1=C(C(=CC=C1)F)CN1N=NC(=C1)N1CCCC1 CPMYTQMQHAYCBW-UHFFFAOYSA-N 0.000 claims description 4
- ZGWGCYNBPYSZSZ-UHFFFAOYSA-N 1-[(2,6-difluorophenyl)methyl]-N-ethyltriazol-4-amine Chemical compound FC1=C(C(=CC=C1)F)CN1N=NC(=C1)NCC ZGWGCYNBPYSZSZ-UHFFFAOYSA-N 0.000 claims description 4
- LGUYVJLSFSVQCS-UHFFFAOYSA-N 1-[1-[(2,6-difluorophenyl)methyl]triazol-4-yl]pyrrolidin-2-one Chemical compound FC1=C(C(=CC=C1)F)CN1N=NC(=C1)N1C(CCC1)=O LGUYVJLSFSVQCS-UHFFFAOYSA-N 0.000 claims description 4
- VCJIVTZFFNFAPR-UHFFFAOYSA-N 3-(3-chlorophenyl)-N-[1-[(4-fluorophenyl)methyl]triazol-4-yl]propanamide Chemical compound ClC=1C=C(C=CC=1)CCC(=O)NC=1N=NN(C=1)CC1=CC=C(C=C1)F VCJIVTZFFNFAPR-UHFFFAOYSA-N 0.000 claims description 4
- NRNXAAXFDBUNIO-UHFFFAOYSA-N 3-[1-[(2,6-difluorophenyl)methyl]triazol-4-yl]-1,3-oxazolidin-2-one Chemical compound FC1=C(C(=CC=C1)F)CN1N=NC(=C1)N1C(OCC1)=O NRNXAAXFDBUNIO-UHFFFAOYSA-N 0.000 claims description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- GMDPTANAUWLYIS-SNVBAGLBSA-N (2R)-2-amino-N-[1-[(2,6-difluorophenyl)methyl]triazol-4-yl]-3-hydroxypropanamide Chemical compound N[C@@H](C(=O)NC=1N=NN(C=1)CC1=C(C=CC=C1F)F)CO GMDPTANAUWLYIS-SNVBAGLBSA-N 0.000 claims description 3
- MWJUGFJHNNOBOI-LLVKDONJSA-N (2R)-2-amino-N-[1-[(2,6-difluorophenyl)methyl]triazol-4-yl]-3-methoxypropanamide Chemical compound N[C@@H](C(=O)NC=1N=NN(C=1)CC1=C(C=CC=C1F)F)COC MWJUGFJHNNOBOI-LLVKDONJSA-N 0.000 claims description 3
- LNUWYMZWRDCHDJ-GFCCVEGCSA-N (3R)-N-[1-[(2,6-difluorophenyl)methyl]triazol-4-yl]morpholine-3-carboxamide Chemical compound FC1=C(C(=CC=C1)F)CN1N=NC(=C1)NC(=O)[C@@H]1NCCOC1 LNUWYMZWRDCHDJ-GFCCVEGCSA-N 0.000 claims description 3
- LNUWYMZWRDCHDJ-LBPRGKRZSA-N (3S)-N-[1-[(2,6-difluorophenyl)methyl]triazol-4-yl]morpholine-3-carboxamide Chemical compound FC1=C(C(=CC=C1)F)CN1N=NC(=C1)NC(=O)[C@H]1NCCOC1 LNUWYMZWRDCHDJ-LBPRGKRZSA-N 0.000 claims description 3
- KYKWHQKFTYMZPB-UHFFFAOYSA-N 1-benzyl-N,N-dimethyltriazol-4-amine Chemical compound C(C1=CC=CC=C1)N1N=NC(=C1)N(C)C KYKWHQKFTYMZPB-UHFFFAOYSA-N 0.000 claims description 3
- OMFJOFLCNIPYCO-UHFFFAOYSA-N N-[1-[(2,6-difluorophenyl)methyl]triazol-4-yl]-3-pyridin-3-ylpropanamide Chemical compound FC1=C(CN2N=NC(=C2)NC(CCC=2C=NC=CC=2)=O)C(=CC=C1)F OMFJOFLCNIPYCO-UHFFFAOYSA-N 0.000 claims description 3
- RVIIAZDTPXSBSA-MRXNPFEDSA-N (2R)-2-amino-N-[1-[(2,6-difluorophenyl)methyl]triazol-4-yl]-3-phenylpropanamide Chemical compound N[C@@H](C(=O)NC=1N=NN(C=1)CC1=C(C=CC=C1F)F)CC1=CC=CC=C1 RVIIAZDTPXSBSA-MRXNPFEDSA-N 0.000 claims description 2
- FZHUVAUHGNQVSK-AWEZNQCLSA-N (2S)-N-[1-[(2,6-difluorophenyl)methyl]triazol-4-yl]-2-(2-oxopyrrolidin-1-yl)butanamide Chemical compound FC1=C(C(=CC=C1)F)CN1N=NC(=C1)NC([C@H](CC)N1C(CCC1)=O)=O FZHUVAUHGNQVSK-AWEZNQCLSA-N 0.000 claims description 2
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 40
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- 150000002148 esters Chemical class 0.000 abstract description 5
- 125000001399 1,2,3-triazolyl group Chemical class N1N=NC(=C1)* 0.000 abstract 1
- 206010010904 Convulsion Diseases 0.000 description 111
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 86
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 69
- 238000012360 testing method Methods 0.000 description 57
- 241001465754 Metazoa Species 0.000 description 55
- 241000699670 Mus sp. Species 0.000 description 51
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 48
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 48
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- 241000700159 Rattus Species 0.000 description 37
- 239000007787 solid Substances 0.000 description 36
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
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- 206010044565 Tremor Diseases 0.000 description 27
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 26
- 239000001961 anticonvulsive agent Substances 0.000 description 24
- 239000003814 drug Substances 0.000 description 23
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 22
- 229940079593 drug Drugs 0.000 description 21
- 239000002904 solvent Substances 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
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- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 17
- 150000001412 amines Chemical class 0.000 description 17
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- PYZRQGJRPPTADH-UHFFFAOYSA-N lamotrigine Chemical compound NC1=NC(N)=NN=C1C1=CC=CC(Cl)=C1Cl PYZRQGJRPPTADH-UHFFFAOYSA-N 0.000 description 12
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 11
- VLSMHEGGTFMBBZ-OOZYFLPDSA-N kainic acid Chemical compound CC(=C)[C@H]1CN[C@H](C(O)=O)[C@H]1CC(O)=O VLSMHEGGTFMBBZ-OOZYFLPDSA-N 0.000 description 11
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- 125000005470 propylenyl group Chemical group 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
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- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- HDOUGSFASVGDCS-UHFFFAOYSA-N pyridin-3-ylmethanamine Chemical compound NCC1=CC=CN=C1 HDOUGSFASVGDCS-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
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- 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 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
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- RWWYLEGWBNMMLJ-YSOARWBDSA-N remdesivir Chemical compound NC1=NC=NN2C1=CC=C2[C@]1([C@@H]([C@@H]([C@H](O1)CO[P@](=O)(OC1=CC=CC=C1)N[C@H](C(=O)OCC(CC)CC)C)O)O)C#N RWWYLEGWBNMMLJ-YSOARWBDSA-N 0.000 description 1
- 230000000284 resting effect Effects 0.000 description 1
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- 238000009094 second-line therapy Methods 0.000 description 1
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- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 229960003928 sodium oxybate Drugs 0.000 description 1
- 235000011006 sodium potassium tartrate Nutrition 0.000 description 1
- 238000003797 solvolysis reaction Methods 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
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- 239000008117 stearic acid Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
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- 230000009534 synaptic inhibition Effects 0.000 description 1
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- 239000011975 tartaric acid Substances 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 230000002123 temporal effect Effects 0.000 description 1
- 231100000211 teratogenicity Toxicity 0.000 description 1
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
- 229960002372 tetracaine Drugs 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 description 1
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229960001918 tiagabine Drugs 0.000 description 1
- PBJUNZJWGZTSKL-MRXNPFEDSA-N tiagabine Chemical compound C1=CSC(C(=CCCN2C[C@@H](CCC2)C(O)=O)C2=C(C=CS2)C)=C1C PBJUNZJWGZTSKL-MRXNPFEDSA-N 0.000 description 1
- 238000003354 tissue distribution assay Methods 0.000 description 1
- 231100000816 toxic dose Toxicity 0.000 description 1
- NNBZCPXTIHJBJL-UHFFFAOYSA-N trans-decahydronaphthalene Natural products C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
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- 229960005318 vigabatrin Drugs 0.000 description 1
- PJDFLNIOAUIZSL-UHFFFAOYSA-N vigabatrin Chemical compound C=CC(N)CCC(O)=O PJDFLNIOAUIZSL-UHFFFAOYSA-N 0.000 description 1
- 210000001835 viscera Anatomy 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
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- 229960002911 zonisamide Drugs 0.000 description 1
- UBQNRHZMVUUOMG-UHFFFAOYSA-N zonisamide Chemical compound C1=CC=C2C(CS(=O)(=O)N)=NOC2=C1 UBQNRHZMVUUOMG-UHFFFAOYSA-N 0.000 description 1
- AIFRHYZBTHREPW-UHFFFAOYSA-N β-carboline Chemical class N1=CC=C2C3=CC=CC=C3NC2=C1 AIFRHYZBTHREPW-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
-
- 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
- A61K31/41—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
- A61K31/4192—1,2,3-Triazoles
-
- 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
- A61K31/41—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
- A61K31/42—Oxazoles
- A61K31/422—Oxazoles not condensed and containing further heterocyclic rings
-
- 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
- A61K31/4965—Non-condensed pyrazines
- A61K31/497—Non-condensed pyrazines containing further heterocyclic rings
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/02—Antidotes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Epidemiology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Psychology (AREA)
- Pain & Pain Management (AREA)
- Toxicology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (5)
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| US62/110,415 | 2015-01-30 | ||
| US201562259314P | 2015-11-24 | 2015-11-24 | |
| US62/259,314 | 2015-11-24 | ||
| PCT/US2016/015740 WO2016123533A1 (en) | 2015-01-30 | 2016-01-29 | Substituted triazoles and methods relating thereto |
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| KR20170106470A KR20170106470A (ko) | 2017-09-20 |
| KR102575601B1 true KR102575601B1 (ko) | 2023-09-05 |
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Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HRP20181670T1 (hr) | 2014-06-03 | 2018-12-14 | Idorsia Pharmaceuticals Ltd | Spojevi pirazola i njihova uporaba kao blokatora kalcijevih kanala t-tipa |
| PL3194374T3 (pl) | 2014-09-15 | 2019-01-31 | Idorsia Pharmaceuticals Ltd | Związki triazolowe jako blokery kanału wapniowego typu t |
| LT3250563T (lt) | 2015-01-30 | 2022-04-11 | Neurocrine Biosciences, Inc. | Pakeisti triazolai ir su jais susiję būdai |
| EP3554490B1 (en) | 2016-12-16 | 2022-02-16 | Idorsia Pharmaceuticals Ltd | Pharmaceutical combination comprising a t-type calcium channel blocker |
| TWI808960B (zh) | 2017-02-06 | 2023-07-21 | 瑞士商愛杜西亞製藥有限公司 | 用於合成1-芳基-1-三氟甲基環丙烷之新穎方法 |
| KR102298546B1 (ko) | 2018-10-18 | 2021-09-08 | 에이치케이이노엔 주식회사 | 신규한 n-(이소프로필-트리아졸릴)피리디닐)-헤테로아릴-카르복사미드 유도체 및 이의 용도 |
| CN110669017B (zh) * | 2019-10-11 | 2023-08-04 | 成都麻沸散医药科技有限公司 | 多取代三唑甲酸酯类衍生物及其用途 |
| CN115974799B (zh) * | 2021-10-14 | 2024-08-13 | 成都百裕制药股份有限公司 | 氨基甲酸酯取代的醇衍生物及其在医药上的应用 |
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| WO2009060053A1 (en) | 2007-11-09 | 2009-05-14 | Smithkline Beecham Corporation | 1, 2, 3-triazole derivatives for use as stearoyl-coa desaturase inhibitors |
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| IL50699A0 (en) * | 1975-10-28 | 1976-12-31 | Ici America Inc | Triazole derivatives |
| TW513301B (en) * | 1999-03-01 | 2002-12-11 | Novartis Ag | Pharmaceutical composition for treatment of neuropathic pain and affective and attention disorders |
| HRP20050053A2 (en) * | 2002-09-19 | 2005-04-30 | Solvay Pharmaceuticals B.V. | 1 h-1,2,4-triazole-3-carboxamide derivatives as cannabinoid-cb1 receptor ligands |
| EP1829867A1 (en) * | 2006-03-03 | 2007-09-05 | Laboratorios Del Dr. Esteve, S.A. | Imidazole compounds having pharmaceutical activity towards the sigma receptor |
| EP1921073A1 (en) * | 2006-11-10 | 2008-05-14 | Laboratorios del Dr. Esteve S.A. | 1,2,4-Triazole derivatives as sigma receptor inhibitors |
| EP1921071A1 (en) * | 2006-11-10 | 2008-05-14 | Laboratorios del Dr. Esteve S.A. | 1,2,3- triazole derivatives as sigma receptor inhibitors |
| US8742097B2 (en) | 2010-11-09 | 2014-06-03 | Hoffmann-La Roche Inc. | Triazole compounds I |
| EP2752411A1 (en) * | 2013-01-07 | 2014-07-09 | Laboratorios Del Dr. Esteve, S.A. | 1,2,3-triazole-4-amine derivatives for the treatment of sigma receptor related diseases and disorders |
| LT3250563T (lt) | 2015-01-30 | 2022-04-11 | Neurocrine Biosciences, Inc. | Pakeisti triazolai ir su jais susiję būdai |
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009060053A1 (en) | 2007-11-09 | 2009-05-14 | Smithkline Beecham Corporation | 1, 2, 3-triazole derivatives for use as stearoyl-coa desaturase inhibitors |
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| Publication | Publication Date | Title |
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