DE69930397T2 - Indazolderivate mit 5-ht2-rezeptor-aktivität - Google Patents
Indazolderivate mit 5-ht2-rezeptor-aktivität Download PDFInfo
- Publication number
- DE69930397T2 DE69930397T2 DE69930397T DE69930397T DE69930397T2 DE 69930397 T2 DE69930397 T2 DE 69930397T2 DE 69930397 T DE69930397 T DE 69930397T DE 69930397 T DE69930397 T DE 69930397T DE 69930397 T2 DE69930397 T2 DE 69930397T2
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- compound according
- disorders
- hydrogen
- compound
- 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.)
- Expired - Fee Related
Links
- 230000000694 effects Effects 0.000 title description 4
- 108091005479 5-HT2 receptors Proteins 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 86
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 33
- -1 monoalkylamino Chemical group 0.000 claims abstract description 29
- 239000001257 hydrogen Substances 0.000 claims abstract description 22
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 18
- 125000003118 aryl group Chemical group 0.000 claims abstract description 17
- 238000011282 treatment Methods 0.000 claims abstract description 17
- 208000008589 Obesity Diseases 0.000 claims abstract description 16
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 16
- 235000020824 obesity Nutrition 0.000 claims abstract description 16
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 14
- 150000002367 halogens Chemical group 0.000 claims abstract description 14
- 208000035475 disorder Diseases 0.000 claims abstract description 13
- 150000003839 salts Chemical class 0.000 claims abstract description 13
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 9
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 8
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 8
- 210000003169 central nervous system Anatomy 0.000 claims abstract description 7
- MBVFRSJFKMJRHA-UHFFFAOYSA-N 4-fluoro-1-benzofuran-7-carbaldehyde Chemical group FC1=CC=C(C=O)C2=C1C=CO2 MBVFRSJFKMJRHA-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims abstract description 6
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract description 6
- 125000005129 aryl carbonyl group Chemical group 0.000 claims abstract description 6
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims abstract description 6
- 125000005110 aryl thio group Chemical group 0.000 claims abstract description 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 6
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 6
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 6
- 208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 5
- 125000005202 dialkylaminocarbonyloxy group Chemical group 0.000 claims abstract description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 5
- 208000018522 Gastrointestinal disease Diseases 0.000 claims abstract description 4
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims abstract description 4
- 201000002859 sleep apnea Diseases 0.000 claims abstract description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 238000011321 prophylaxis Methods 0.000 claims description 6
- 230000001225 therapeutic effect Effects 0.000 claims description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 208000015114 central nervous system disease Diseases 0.000 claims description 5
- 201000010099 disease Diseases 0.000 claims description 5
- 229940079593 drug Drugs 0.000 claims description 5
- 125000001188 haloalkyl group Chemical group 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 230000003542 behavioural effect Effects 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
- AZGLXCKHALIYEZ-UHFFFAOYSA-N 1-(3-ethyl-6-methylsulfanylindazol-1-yl)propan-2-amine Chemical compound CSC1=CC=C2C(CC)=NN(CC(C)N)C2=C1 AZGLXCKHALIYEZ-UHFFFAOYSA-N 0.000 claims description 3
- QGDUUJDJXSDKCP-UHFFFAOYSA-N 1-(6-bromo-3-ethylindazol-1-yl)propan-2-amine Chemical compound BrC1=CC=C2C(CC)=NN(CC(C)N)C2=C1 QGDUUJDJXSDKCP-UHFFFAOYSA-N 0.000 claims description 3
- 201000009906 Meningitis Diseases 0.000 claims description 3
- 125000002015 acyclic group Chemical group 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 206010014599 encephalitis Diseases 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 3
- 208000015181 infectious disease Diseases 0.000 claims description 3
- 230000002458 infectious effect Effects 0.000 claims description 3
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 3
- 231100000331 toxic Toxicity 0.000 claims description 3
- 230000002588 toxic effect Effects 0.000 claims description 3
- DRLGTCNDEBEPQP-UHFFFAOYSA-N 1-(5,6-difluoro-3-methylindazol-1-yl)propan-2-amine Chemical compound FC1=C(F)C=C2N(CC(N)C)N=C(C)C2=C1 DRLGTCNDEBEPQP-UHFFFAOYSA-N 0.000 claims description 2
- PKGIAAHUVWWFPM-UHFFFAOYSA-N 1-(6-chloro-5-fluoro-3-methylindazol-1-yl)propan-2-amine Chemical compound FC1=C(Cl)C=C2N(CC(N)C)N=C(C)C2=C1 PKGIAAHUVWWFPM-UHFFFAOYSA-N 0.000 claims description 2
- WMYZYDUOEKWORM-UHFFFAOYSA-N 1-(6-methoxy-3-methylindazol-1-yl)propan-2-amine Chemical compound COC1=CC=C2C(C)=NN(CC(C)N)C2=C1 WMYZYDUOEKWORM-UHFFFAOYSA-N 0.000 claims description 2
- OCJCKHPFQNWROT-UHFFFAOYSA-N 1-[3-ethyl-6-(trifluoromethyl)indazol-1-yl]propan-2-amine Chemical compound FC(F)(F)C1=CC=C2C(CC)=NN(CC(C)N)C2=C1 OCJCKHPFQNWROT-UHFFFAOYSA-N 0.000 claims description 2
- 206010001488 Aggression Diseases 0.000 claims description 2
- 208000007848 Alcoholism Diseases 0.000 claims description 2
- 208000019901 Anxiety disease Diseases 0.000 claims description 2
- 208000020925 Bipolar disease Diseases 0.000 claims description 2
- 208000032841 Bulimia Diseases 0.000 claims description 2
- 206010006550 Bulimia nervosa Diseases 0.000 claims description 2
- 206010008874 Chronic Fatigue Syndrome Diseases 0.000 claims description 2
- 206010012289 Dementia Diseases 0.000 claims description 2
- 206010019233 Headaches Diseases 0.000 claims description 2
- 206010022773 Intracranial pressure increased Diseases 0.000 claims description 2
- 208000026139 Memory disease Diseases 0.000 claims description 2
- 208000019695 Migraine disease Diseases 0.000 claims description 2
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 2
- 208000002193 Pain Diseases 0.000 claims description 2
- 206010036618 Premenstrual syndrome Diseases 0.000 claims description 2
- 208000028017 Psychotic disease Diseases 0.000 claims description 2
- 201000001880 Sexual dysfunction Diseases 0.000 claims description 2
- 206010041250 Social phobia Diseases 0.000 claims description 2
- 208000006011 Stroke Diseases 0.000 claims description 2
- 208000007536 Thrombosis Diseases 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 2
- 125000005093 alkyl carbonyl alkyl group Chemical group 0.000 claims description 2
- 125000005197 alkyl carbonyloxy alkyl group Chemical group 0.000 claims description 2
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 2
- 125000004687 alkyl sulfinyl alkyl group Chemical group 0.000 claims description 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
- 125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 claims description 2
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 2
- 125000005097 aminocarbonylalkyl group Chemical group 0.000 claims description 2
- 208000022531 anorexia Diseases 0.000 claims description 2
- 125000005099 aryl alkyl carbonyl group Chemical group 0.000 claims description 2
- 125000005100 aryl amino carbonyl group Chemical group 0.000 claims description 2
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 2
- 125000005162 aryl oxy carbonyl amino group Chemical group 0.000 claims description 2
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims description 2
- 125000005164 aryl thioalkyl group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 208000025748 atypical depressive disease Diseases 0.000 claims description 2
- 125000002393 azetidinyl group Chemical group 0.000 claims description 2
- 150000001540 azides Chemical class 0.000 claims description 2
- 125000004069 aziridinyl group Chemical group 0.000 claims description 2
- 125000004619 benzopyranyl group Chemical group O1C(C=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004622 benzoxazinyl group Chemical group O1NC(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004623 carbolinyl group Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 2
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims description 2
- 125000004230 chromenyl group Chemical group O1C(C=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000000332 coumarinyl group Chemical group O1C(=O)C(=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 2
- 206010061428 decreased appetite Diseases 0.000 claims description 2
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 2
- 206010013663 drug dependence Diseases 0.000 claims description 2
- 206010015037 epilepsy Diseases 0.000 claims description 2
- 230000005176 gastrointestinal motility Effects 0.000 claims description 2
- 231100000869 headache Toxicity 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000004634 hexahydroazepinyl group Chemical group N1(CCCCCC1)* 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 125000002632 imidazolidinyl group Chemical group 0.000 claims description 2
- 125000002636 imidazolinyl group Chemical group 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 2
- 125000001041 indolyl group Chemical group 0.000 claims description 2
- 208000014674 injury Diseases 0.000 claims description 2
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 claims description 2
- 125000003384 isochromanyl group Chemical group C1(OCCC2=CC=CC=C12)* 0.000 claims description 2
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 2
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 2
- 206010027599 migraine Diseases 0.000 claims description 2
- 125000002757 morpholinyl group Chemical group 0.000 claims description 2
- 208000029766 myalgic encephalomeyelitis/chronic fatigue syndrome Diseases 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 230000004770 neurodegeneration Effects 0.000 claims description 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 2
- 125000002971 oxazolyl group Chemical group 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 208000022821 personality disease Diseases 0.000 claims description 2
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000004193 piperazinyl group Chemical group 0.000 claims description 2
- 125000005936 piperidyl group Chemical group 0.000 claims description 2
- 208000020016 psychiatric disease Diseases 0.000 claims description 2
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
- 125000003072 pyrazolidinyl group Chemical group 0.000 claims description 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 2
- 125000004590 pyridopyridyl group Chemical group N1=C(C=CC2=C1C=CC=N2)* 0.000 claims description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
- 125000001422 pyrrolinyl group Chemical group 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 201000000980 schizophrenia Diseases 0.000 claims description 2
- 231100000872 sexual dysfunction Toxicity 0.000 claims description 2
- 208000019116 sleep disease Diseases 0.000 claims description 2
- 208000011117 substance-related disease Diseases 0.000 claims description 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 2
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- 230000008733 trauma Effects 0.000 claims description 2
- 208000010643 digestive system disease Diseases 0.000 claims 2
- 208000018685 gastrointestinal system disease Diseases 0.000 claims 2
- 208000027626 Neurocognitive disease Diseases 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 230000007257 malfunction Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 102100026383 Vasopressin-neurophysin 2-copeptin Human genes 0.000 abstract 1
- 201000010064 diabetes insipidus Diseases 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 229940002612 prodrug Drugs 0.000 abstract 1
- 239000000651 prodrug Substances 0.000 abstract 1
- 238000002560 therapeutic procedure Methods 0.000 abstract 1
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 52
- 238000000034 method Methods 0.000 description 37
- 239000000203 mixture Substances 0.000 description 27
- 239000000047 product Substances 0.000 description 25
- 239000007787 solid Substances 0.000 description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 20
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
- 102000005962 receptors Human genes 0.000 description 15
- 108020003175 receptors Proteins 0.000 description 15
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 8
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 8
- 235000019341 magnesium sulphate Nutrition 0.000 description 8
- 239000002585 base Substances 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- VHFVKMTVMIZMIK-UHFFFAOYSA-N 1-(3-chlorophenyl)piperazine Chemical compound ClC1=CC=CC(N2CCNCC2)=C1 VHFVKMTVMIZMIK-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 229910004298 SiO 2 Inorganic materials 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- DEQYTNZJHKPYEZ-UHFFFAOYSA-N ethyl acetate;heptane Chemical compound CCOC(C)=O.CCCCCCC DEQYTNZJHKPYEZ-UHFFFAOYSA-N 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 150000002473 indoazoles Chemical class 0.000 description 5
- 239000000018 receptor agonist Substances 0.000 description 5
- 229940044601 receptor agonist Drugs 0.000 description 5
- 230000004580 weight loss Effects 0.000 description 5
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000012230 colorless oil Substances 0.000 description 4
- 230000037406 food intake Effects 0.000 description 4
- 235000012631 food intake Nutrition 0.000 description 4
- 239000012458 free base Substances 0.000 description 4
- 150000007857 hydrazones Chemical class 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- DBGIVFWFUFKIQN-UHFFFAOYSA-N (+-)-Fenfluramine Chemical compound CCNC(C)CC1=CC=CC(C(F)(F)F)=C1 DBGIVFWFUFKIQN-UHFFFAOYSA-N 0.000 description 3
- VLXNUECYZIBLQO-LOOJJACZSA-N (2s)-1-(6-bromo-3-ethylindazol-1-yl)propan-2-amine;(e)-but-2-enedioic acid Chemical compound OC(=O)\C=C\C(O)=O.BrC1=CC=C2C(CC)=NN(C[C@H](C)N)C2=C1 VLXNUECYZIBLQO-LOOJJACZSA-N 0.000 description 3
- VXVKSDKSDIJAQR-LOOJJACZSA-N (e)-but-2-enedioic acid;(2s)-1-(3-ethyl-6-fluoroindazol-1-yl)propan-2-amine Chemical compound OC(=O)\C=C\C(O)=O.FC1=CC=C2C(CC)=NN(C[C@H](C)N)C2=C1 VXVKSDKSDIJAQR-LOOJJACZSA-N 0.000 description 3
- INUVPPOOSRNHAQ-AFIAKLHKSA-N (e)-but-2-enedioic acid;(2s)-1-(3-ethyl-6-methylsulfanylindazol-1-yl)propan-2-amine Chemical compound OC(=O)\C=C\C(O)=O.CSC1=CC=C2C(CC)=NN(C[C@H](C)N)C2=C1 INUVPPOOSRNHAQ-AFIAKLHKSA-N 0.000 description 3
- YHOSRFAOWUAFLC-UHMUWMDISA-N (e)-but-2-enedioic acid;(2s)-1-(5,6-difluoro-3-methylindazol-1-yl)propan-2-amine Chemical compound OC(=O)\C=C\C(O)=O.FC1=C(F)C=C2N(C[C@@H](N)C)N=C(C)C2=C1 YHOSRFAOWUAFLC-UHMUWMDISA-N 0.000 description 3
- RWWWRPVVYDFQHF-UHMUWMDISA-N (e)-but-2-enedioic acid;(2s)-1-(6-chloro-5-fluoro-3-methylindazol-1-yl)propan-2-amine Chemical compound OC(=O)\C=C\C(O)=O.FC1=C(Cl)C=C2N(C[C@@H](N)C)N=C(C)C2=C1 RWWWRPVVYDFQHF-UHMUWMDISA-N 0.000 description 3
- FGQUUCRNAOILHX-LOOJJACZSA-N (e)-but-2-enedioic acid;(2s)-1-(6-methoxy-3-methylindazol-1-yl)propan-2-amine Chemical compound OC(=O)\C=C\C(O)=O.COC1=CC=C2C(C)=NN(C[C@H](C)N)C2=C1 FGQUUCRNAOILHX-LOOJJACZSA-N 0.000 description 3
- QSEUAOJEUKLACV-LOOJJACZSA-N (e)-but-2-enedioic acid;(2s)-1-[3-ethyl-6-(trifluoromethyl)indazol-1-yl]propan-2-amine Chemical compound OC(=O)\C=C\C(O)=O.FC(F)(F)C1=CC=C2C(CC)=NN(C[C@H](C)N)C2=C1 QSEUAOJEUKLACV-LOOJJACZSA-N 0.000 description 3
- ICWGBAFJCUHSHX-UHFFFAOYSA-N 3-ethyl-6-fluoro-2h-indazole Chemical compound FC1=CC=C2C(CC)=NNC2=C1 ICWGBAFJCUHSHX-UHFFFAOYSA-N 0.000 description 3
- AYKFFGFHDFHWJV-UHFFFAOYSA-N 3-ethyl-6-methylsulfanyl-2h-indazole Chemical compound CSC1=CC=C2C(CC)=NNC2=C1 AYKFFGFHDFHWJV-UHFFFAOYSA-N 0.000 description 3
- RFXDXIFAWRAUNL-UHFFFAOYSA-N 5,6-difluoro-3-methyl-2h-indazole Chemical compound FC1=C(F)C=C2C(C)=NNC2=C1 RFXDXIFAWRAUNL-UHFFFAOYSA-N 0.000 description 3
- XZRBYJWQQQBHLP-UHFFFAOYSA-N 6-bromo-3-ethyl-2h-indazole Chemical compound C1=C(Br)C=CC2=C(CC)NN=C21 XZRBYJWQQQBHLP-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical class OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 235000019502 Orange oil Nutrition 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 210000004978 chinese hamster ovary cell Anatomy 0.000 description 3
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 3
- 239000003925 fat Substances 0.000 description 3
- 235000019197 fats Nutrition 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 239000010502 orange oil Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- UNAANXDKBXWMLN-UHFFFAOYSA-N sibutramine Chemical compound C=1C=C(Cl)C=CC=1C1(C(N(C)C)CC(C)C)CCC1 UNAANXDKBXWMLN-UHFFFAOYSA-N 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- 125000006633 tert-butoxycarbonylamino group Chemical group 0.000 description 3
- VRANJNBZEBOJJL-VIFPVBQESA-N tert-butyl n-[(2s)-1-(6-chloro-5-fluoro-3-methylindazol-1-yl)propan-2-yl]carbamate Chemical compound FC1=C(Cl)C=C2N(C[C@H](C)NC(=O)OC(C)(C)C)N=C(C)C2=C1 VRANJNBZEBOJJL-VIFPVBQESA-N 0.000 description 3
- AGETWHIABGMSKU-NSHDSACASA-N tert-butyl n-[(2s)-1-(6-methoxy-3-methylindazol-1-yl)propan-2-yl]carbamate Chemical compound COC1=CC=C2C(C)=NN(C[C@H](C)NC(=O)OC(C)(C)C)C2=C1 AGETWHIABGMSKU-NSHDSACASA-N 0.000 description 3
- 239000003981 vehicle Substances 0.000 description 3
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
- WTDITXJQPYQUMW-WLHGVMLRSA-N (e)-but-2-enedioic acid;1-(3-methylindazol-1-yl)propan-2-amine Chemical compound OC(=O)\C=C\C(O)=O.C1=CC=C2N(CC(N)C)N=C(C)C2=C1 WTDITXJQPYQUMW-WLHGVMLRSA-N 0.000 description 2
- ODZPDKNMMFEYFD-UHFFFAOYSA-N 1-(2-fluoro-4-methylphenyl)propane-1-thione Chemical compound CCC(=S)C1=CC=C(C)C=C1F ODZPDKNMMFEYFD-UHFFFAOYSA-N 0.000 description 2
- VAWRVSQLVIYZRK-UHFFFAOYSA-N 1-(4-bromo-2-fluorophenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(Br)C=C1F VAWRVSQLVIYZRK-UHFFFAOYSA-N 0.000 description 2
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 2
- PLDXUUNKQFWHIU-UHFFFAOYSA-N 3-ethyl-6-(trifluoromethyl)-2h-indazole Chemical compound FC(F)(F)C1=CC=C2C(CC)=NNC2=C1 PLDXUUNKQFWHIU-UHFFFAOYSA-N 0.000 description 2
- 102000040125 5-hydroxytryptamine receptor family Human genes 0.000 description 2
- 108091032151 5-hydroxytryptamine receptor family Proteins 0.000 description 2
- VUWAZPQQDATARH-UHFFFAOYSA-N 6-chloro-5-fluoro-3-methyl-2h-indazole Chemical compound ClC1=C(F)C=C2C(C)=NNC2=C1 VUWAZPQQDATARH-UHFFFAOYSA-N 0.000 description 2
- VDRWFBGSDLRPLK-UHFFFAOYSA-N 6-methoxy-3-methyl-2h-indazole Chemical compound COC1=CC=C2C(C)=NNC2=C1 VDRWFBGSDLRPLK-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 210000000577 adipose tissue Anatomy 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 239000000556 agonist Substances 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 150000004983 alkyl aryl ketones Chemical class 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 239000012131 assay buffer Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 206010012601 diabetes mellitus Diseases 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 229960001582 fenfluramine Drugs 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 230000006870 function Effects 0.000 description 2
- 230000005714 functional activity Effects 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- AHLBNYSZXLDEJQ-FWEHEUNISA-N orlistat Chemical compound CCCCCCCCCCC[C@H](OC(=O)[C@H](CC(C)C)NC=O)C[C@@H]1OC(=O)[C@H]1CCCCCC AHLBNYSZXLDEJQ-FWEHEUNISA-N 0.000 description 2
- 229960001243 orlistat Drugs 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 229960004425 sibutramine Drugs 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- QTHVURQESVNUSF-NSHDSACASA-N tert-butyl n-[(2s)-1-(3-ethyl-6-fluoroindazol-1-yl)propan-2-yl]carbamate Chemical compound FC1=CC=C2C(CC)=NN(C[C@H](C)NC(=O)OC(C)(C)C)C2=C1 QTHVURQESVNUSF-NSHDSACASA-N 0.000 description 2
- UTHAYPVGFLSIKQ-VIFPVBQESA-N tert-butyl n-[(2s)-1-(5,6-difluoro-3-methylindazol-1-yl)propan-2-yl]carbamate Chemical compound FC1=C(F)C=C2N(C[C@H](C)NC(=O)OC(C)(C)C)N=C(C)C2=C1 UTHAYPVGFLSIKQ-VIFPVBQESA-N 0.000 description 2
- YWHQLZIUOJXDJU-UHFFFAOYSA-N tert-butyl n-[1-(3-methylindazol-1-yl)propan-2-yl]carbamate Chemical compound C1=CC=C2N(CC(C)NC(=O)OC(C)(C)C)N=C(C)C2=C1 YWHQLZIUOJXDJU-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- DBGIVFWFUFKIQN-VIFPVBQESA-N (+)-Fenfluramine Chemical compound CCN[C@@H](C)CC1=CC=CC(C(F)(F)F)=C1 DBGIVFWFUFKIQN-VIFPVBQESA-N 0.000 description 1
- HFVMEOPYDLEHBR-UHFFFAOYSA-N (2-fluorophenyl)-phenylmethanol Chemical compound C=1C=CC=C(F)C=1C(O)C1=CC=CC=C1 HFVMEOPYDLEHBR-UHFFFAOYSA-N 0.000 description 1
- DDMOUSALMHHKOS-UHFFFAOYSA-N 1,2-dichloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)(Cl)C(F)(F)Cl DDMOUSALMHHKOS-UHFFFAOYSA-N 0.000 description 1
- QUERAHCHJWZYJF-UHFFFAOYSA-N 1-(1h-indol-2-yl)ethanamine Chemical class C1=CC=C2NC(C(N)C)=CC2=C1 QUERAHCHJWZYJF-UHFFFAOYSA-N 0.000 description 1
- IVZCHEJTIUBJPM-UHFFFAOYSA-N 1-(1h-pyrazol-5-yl)ethanamine Chemical class CC(N)C1=CC=NN1 IVZCHEJTIUBJPM-UHFFFAOYSA-N 0.000 description 1
- KYCDNQPIQHCAFW-UHFFFAOYSA-N 1-(1h-pyrrol-2-yl)ethanamine Chemical class CC(N)C1=CC=CN1 KYCDNQPIQHCAFW-UHFFFAOYSA-N 0.000 description 1
- UZWOADNMVRRYDE-UHFFFAOYSA-N 1-(2,4-difluorophenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(F)C=C1F UZWOADNMVRRYDE-UHFFFAOYSA-N 0.000 description 1
- PIRRWUMTIBFCCW-UHFFFAOYSA-N 1-(2-fluoro-4-methoxyphenyl)ethanone Chemical compound COC1=CC=C(C(C)=O)C(F)=C1 PIRRWUMTIBFCCW-UHFFFAOYSA-N 0.000 description 1
- KKIMDKMETPPURN-UHFFFAOYSA-N 1-(3-(trifluoromethyl)phenyl)piperazine Chemical compound FC(F)(F)C1=CC=CC(N2CCNCC2)=C1 KKIMDKMETPPURN-UHFFFAOYSA-N 0.000 description 1
- XLBICEUZJHYFQG-UHFFFAOYSA-N 1-(4-chloro-2,5-difluorophenyl)ethanone Chemical compound CC(=O)C1=CC(F)=C(Cl)C=C1F XLBICEUZJHYFQG-UHFFFAOYSA-N 0.000 description 1
- PDWYVBFOPQMCLP-UHFFFAOYSA-N 1-[2-fluoro-4-(trifluoromethyl)phenyl]propan-1-one Chemical compound CCC(=O)C1=CC=C(C(F)(F)F)C=C1F PDWYVBFOPQMCLP-UHFFFAOYSA-N 0.000 description 1
- DGNLGWJZZZOYPT-UHFFFAOYSA-N 1-[3-(trifluoromethyl)phenyl]piperazin-1-ium;chloride Chemical compound [Cl-].FC(F)(F)C1=CC=CC(N2CC[NH2+]CC2)=C1 DGNLGWJZZZOYPT-UHFFFAOYSA-N 0.000 description 1
- QDFKKJYEIFBEFC-UHFFFAOYSA-N 1-bromo-3-fluorobenzene Chemical compound FC1=CC=CC(Br)=C1 QDFKKJYEIFBEFC-UHFFFAOYSA-N 0.000 description 1
- SQXSNYMCORGWCE-UHFFFAOYSA-N 1-fluoro-3-methylsulfanylbenzene Chemical compound CSC1=CC=CC(F)=C1 SQXSNYMCORGWCE-UHFFFAOYSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 1
- GYGXGLJCAHRRLQ-UHFFFAOYSA-N 3-amino-3-oxopropane-1-sulfonic acid Chemical compound NC(=O)CCS(O)(=O)=O GYGXGLJCAHRRLQ-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- NCVGVDSQMXKWGU-UHFFFAOYSA-N 3-azido-1h-indazole Chemical compound C1=CC=C2C(N=[N+]=[N-])=NNC2=C1 NCVGVDSQMXKWGU-UHFFFAOYSA-N 0.000 description 1
- FWOPJXVQGMZKEP-UHFFFAOYSA-N 3-methyl-2h-indazole Chemical compound C1=CC=CC2=C(C)NN=C21 FWOPJXVQGMZKEP-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- QISOBCMNUJQOJU-UHFFFAOYSA-N 4-bromo-1h-pyrazole-5-carboxylic acid Chemical compound OC(=O)C=1NN=CC=1Br QISOBCMNUJQOJU-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 235000019489 Almond oil Nutrition 0.000 description 1
- 244000144725 Amygdalus communis Species 0.000 description 1
- 235000011437 Amygdalus communis Nutrition 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- 206010012735 Diarrhoea Diseases 0.000 description 1
- 239000004338 Dichlorodifluoromethane Substances 0.000 description 1
- 241000792859 Enema Species 0.000 description 1
- OZLGRUXZXMRXGP-UHFFFAOYSA-N Fluo-3 Chemical compound CC1=CC=C(N(CC(O)=O)CC(O)=O)C(OCCOC=2C(=CC=C(C=2)C2=C3C=C(Cl)C(=O)C=C3OC3=CC(O)=C(Cl)C=C32)N(CC(O)=O)CC(O)=O)=C1 OZLGRUXZXMRXGP-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- 240000007472 Leucaena leucocephala Species 0.000 description 1
- 229940086609 Lipase inhibitor Drugs 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 206010033307 Overweight Diseases 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- MZILPZDBVFUXMY-UHFFFAOYSA-N [O-][N+]([S])=O Chemical compound [O-][N+]([S])=O MZILPZDBVFUXMY-UHFFFAOYSA-N 0.000 description 1
- 230000005856 abnormality Effects 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 235000020224 almond Nutrition 0.000 description 1
- 239000008168 almond oil Substances 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000001539 anorectic effect Effects 0.000 description 1
- 230000003579 anti-obesity Effects 0.000 description 1
- 239000000883 anti-obesity agent Substances 0.000 description 1
- 235000019789 appetite Nutrition 0.000 description 1
- 230000036528 appetite Effects 0.000 description 1
- 235000021229 appetite regulation Nutrition 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000005002 aryl methyl group Chemical group 0.000 description 1
- 238000011914 asymmetric synthesis Methods 0.000 description 1
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 230000006399 behavior Effects 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 229960004424 carbon dioxide Drugs 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 208000029078 coronary artery disease Diseases 0.000 description 1
- 229960004597 dexfenfluramine Drugs 0.000 description 1
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
- 229940042935 dichlorodifluoromethane Drugs 0.000 description 1
- 229940087091 dichlorotetrafluoroethane Drugs 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 230000004064 dysfunction Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000007920 enema Substances 0.000 description 1
- 229940079360 enema for constipation Drugs 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 208000020694 gallbladder disease Diseases 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 210000003709 heart valve Anatomy 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 125000003151 isocoumarinyl group Chemical group C1(=O)OC(=CC2=CC=CC=C12)* 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 230000004630 mental health Effects 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- LAIZPRYFQUWUBN-UHFFFAOYSA-L nickel chloride hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].[Cl-].[Ni+2] LAIZPRYFQUWUBN-UHFFFAOYSA-L 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000002687 nonaqueous vehicle Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000002767 noradrenalin uptake inhibitor Substances 0.000 description 1
- 229940127221 norepinephrine reuptake inhibitor Drugs 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000004031 partial agonist Substances 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- DBABZHXKTCFAPX-UHFFFAOYSA-N probenecid Chemical compound CCCN(CCC)S(=O)(=O)C1=CC=C(C(O)=O)C=C1 DBABZHXKTCFAPX-UHFFFAOYSA-N 0.000 description 1
- 229960003081 probenecid Drugs 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical class CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 235000018770 reduced food intake Nutrition 0.000 description 1
- 238000005932 reductive alkylation reaction Methods 0.000 description 1
- 230000001850 reproductive effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 230000036186 satiety Effects 0.000 description 1
- 235000019627 satiety Nutrition 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- 239000002484 serotonin 2C antagonist Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 229940079832 sodium starch glycolate Drugs 0.000 description 1
- 239000008109 sodium starch glycolate Substances 0.000 description 1
- 229920003109 sodium starch glycolate Polymers 0.000 description 1
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- DJJPIYHRBNYKPD-LBPRGKRZSA-N tert-butyl n-[(2s)-1-(3-ethyl-6-methylsulfanylindazol-1-yl)propan-2-yl]carbamate Chemical compound CSC1=CC=C2C(CC)=NN(C[C@H](C)NC(=O)OC(C)(C)C)C2=C1 DJJPIYHRBNYKPD-LBPRGKRZSA-N 0.000 description 1
- HGWNCYKSRLMHBY-NSHDSACASA-N tert-butyl n-[(2s)-1-(6-bromo-3-ethylindazol-1-yl)propan-2-yl]carbamate Chemical compound BrC1=CC=C2C(CC)=NN(C[C@H](C)NC(=O)OC(C)(C)C)C2=C1 HGWNCYKSRLMHBY-NSHDSACASA-N 0.000 description 1
- PKBDCMUHKYUWJE-NSHDSACASA-N tert-butyl n-[(2s)-1-[3-ethyl-6-(trifluoromethyl)indazol-1-yl]propan-2-yl]carbamate Chemical compound FC(F)(F)C1=CC=C2C(CC)=NN(C[C@H](C)NC(=O)OC(C)(C)C)C2=C1 PKBDCMUHKYUWJE-NSHDSACASA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary 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
-
- 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
- A61P25/06—Antimigraine agents
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- 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
- A61P25/22—Anxiolytics
-
- 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
- A61P25/24—Antidepressants
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/32—Alcohol-abuse
-
- 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
- A61P3/04—Anorexiants; Antiobesity 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
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Psychiatry (AREA)
- Diabetes (AREA)
- Pain & Pain Management (AREA)
- Addiction (AREA)
- Hematology (AREA)
- Cardiology (AREA)
- Child & Adolescent Psychology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Obesity (AREA)
- Anesthesiology (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9819032 | 1998-09-01 | ||
| GBGB9819032.5A GB9819032D0 (en) | 1998-09-01 | 1998-09-01 | Chemical compounds IV |
| PCT/GB1999/002875 WO2000012481A2 (en) | 1998-09-01 | 1999-09-01 | Indazole derivatives with 5-ht2 receptor activity________________ |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69930397D1 DE69930397D1 (de) | 2006-05-11 |
| DE69930397T2 true DE69930397T2 (de) | 2006-11-30 |
Family
ID=10838164
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69930397T Expired - Fee Related DE69930397T2 (de) | 1998-09-01 | 1999-09-01 | Indazolderivate mit 5-ht2-rezeptor-aktivität |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US6552062B1 (enExample) |
| EP (1) | EP1129078B1 (enExample) |
| JP (1) | JP2002525280A (enExample) |
| AT (1) | ATE320419T1 (enExample) |
| AU (1) | AU5636799A (enExample) |
| CA (1) | CA2341612A1 (enExample) |
| DE (1) | DE69930397T2 (enExample) |
| ES (1) | ES2260931T3 (enExample) |
| GB (1) | GB9819032D0 (enExample) |
| WO (1) | WO2000012481A2 (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9820767D0 (en) * | 1998-09-23 | 1998-11-18 | Cerebrus Ltd | Chemical compounds VIII |
| GB9902047D0 (en) * | 1999-01-29 | 1999-03-17 | Cerebrus Ltd | Chemical compounds XI |
| US6956036B1 (en) * | 2000-03-17 | 2005-10-18 | Alcon, Inc. | 6-hydroxy-indazole derivatives for treating glaucoma |
| AU2001216072A1 (en) * | 2000-03-17 | 2001-10-03 | Alcon, Inc. | 6-hydroxy-indazole derivatives for treating glaucoma |
| SE0004245D0 (sv) | 2000-11-20 | 2000-11-20 | Pharmacia Ab | Novel compounds and their use |
| DE60139021D1 (de) | 2000-11-20 | 2009-07-30 | Biovitrum Ab Publ | Piperazinylpyrazinverbindungen als antagonisten des serotonin-5-ht2-rezeptors |
| JP2005506280A (ja) | 2000-12-20 | 2005-03-03 | ブリストル−マイヤーズ・スクイブ・ファーマ・カンパニー | アリールおよびアミノアリール置換セロトニン受容体アゴニストおよびアンタゴニストリガンド |
| AU2002360819A1 (en) * | 2001-12-28 | 2003-07-24 | Bayer Corporation | Cyclohexano- and cycloheptapyrazole derivative compounds, for use in diseases associated with the 5-ht2c receptor |
| TW200400177A (en) * | 2002-06-04 | 2004-01-01 | Wyeth Corp | 1-(Aminoalkyl)-3-sulfonylindole and-indazole derivatives as 5-hydroxytryptamine-6 ligands |
| EP1513831B1 (en) | 2002-06-19 | 2010-01-06 | Biovitrum AB (publ) | Novel compounds, their use and preparation |
| CL2004000826A1 (es) | 2003-04-25 | 2005-03-04 | Pfizer | Uso de un agonista para el receptor 5-ht2c para preparar un medicamento util en el tratamiento de la incontinencia urinaria provocada por estres, con la condicion de que el agonista no sea 1-[6-cloro-5-(trifluorometil)-2-piridinil]piperazina (org-129 |
| GB0314967D0 (en) * | 2003-06-26 | 2003-07-30 | Hoffmann La Roche | Piperazine derivatives |
| EP2400300A1 (en) | 2004-08-25 | 2011-12-28 | Takeda Pharmaceutical Company Limited | Method of screening preventives/remedies for stress urinary incontinence |
| WO2007132841A1 (ja) | 2006-05-16 | 2007-11-22 | Takeda Pharmaceutical Company Limited | 縮合複素環化合物およびその用途 |
| JP5520051B2 (ja) | 2007-11-15 | 2014-06-11 | 武田薬品工業株式会社 | 縮合ピリジン誘導体およびその用途 |
| JPWO2011071136A1 (ja) | 2009-12-11 | 2013-04-22 | アステラス製薬株式会社 | 線維筋痛症治療剤 |
| WO2015066344A1 (en) | 2013-11-01 | 2015-05-07 | Arena Pharmaceuticals, Inc. | 5-ht2c receptor agonists and compositions and methods of use |
| US20210052600A1 (en) | 2017-12-27 | 2021-02-25 | Takeda Pharmaceutical Company Limited | Therapeutic agents for stress urinary incontinence and incotinence of feces |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0232059A (ja) * | 1988-07-18 | 1990-02-01 | Kyowa Hakko Kogyo Co Ltd | インダゾール誘導体 |
| US5187166A (en) * | 1990-07-31 | 1993-02-16 | Nisshin Flour Milling Co., Ltd. | Azabicyclo derivatives and their use as antiemetics |
| TW270114B (enExample) * | 1993-10-22 | 1996-02-11 | Hoffmann La Roche | |
| JPH08225535A (ja) * | 1994-11-15 | 1996-09-03 | Dai Ichi Seiyaku Co Ltd | インダゾール誘導体 |
| AU5343298A (en) * | 1997-01-13 | 1998-08-03 | Yamanouchi Pharmaceutical Co., Ltd. | 5-ht2c receptor agonists and aminoalkylindazole derivatives |
-
1998
- 1998-09-01 GB GBGB9819032.5A patent/GB9819032D0/en not_active Ceased
-
1999
- 1999-09-01 DE DE69930397T patent/DE69930397T2/de not_active Expired - Fee Related
- 1999-09-01 JP JP2000571048A patent/JP2002525280A/ja active Pending
- 1999-09-01 EP EP99943082A patent/EP1129078B1/en not_active Expired - Lifetime
- 1999-09-01 WO PCT/GB1999/002875 patent/WO2000012481A2/en not_active Ceased
- 1999-09-01 US US09/763,886 patent/US6552062B1/en not_active Expired - Fee Related
- 1999-09-01 AT AT99943082T patent/ATE320419T1/de not_active IP Right Cessation
- 1999-09-01 CA CA002341612A patent/CA2341612A1/en not_active Abandoned
- 1999-09-01 AU AU56367/99A patent/AU5636799A/en not_active Abandoned
- 1999-09-01 ES ES99943082T patent/ES2260931T3/es not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| ES2260931T3 (es) | 2006-11-01 |
| ATE320419T1 (de) | 2006-04-15 |
| JP2002525280A (ja) | 2002-08-13 |
| AU5636799A (en) | 2000-03-21 |
| CA2341612A1 (en) | 2000-03-09 |
| WO2000012481A2 (en) | 2000-03-09 |
| DE69930397D1 (de) | 2006-05-11 |
| WO2000012481A3 (en) | 2000-06-08 |
| GB9819032D0 (en) | 1998-10-28 |
| US6552062B1 (en) | 2003-04-22 |
| EP1129078B1 (en) | 2006-03-15 |
| EP1129078A2 (en) | 2001-09-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE60002554T2 (de) | Pyrazino(aza)indolderivate | |
| DE69930397T2 (de) | Indazolderivate mit 5-ht2-rezeptor-aktivität | |
| DE60014918T2 (de) | Indol-verbindungen, verfahren zu ihrer herstellung, sie enthaltende pharmazeutische zusammensetzungen und ihre medizinische anwendung | |
| DE69919364T2 (de) | Pyrroloindole, pyridoindole und azepinoindole als 5-ht2c agonisten | |
| DE69922024T2 (de) | Pyrrolochinoline zur Behandlung von Fettleibigkeit | |
| DE60119719T2 (de) | Neue aza-indolyl derivate | |
| DE60218037T2 (de) | Neue indolderivate mit affinität zum 5-ht6-rezeptor | |
| CN101248041B (zh) | 鞘氨醇激酶抑制剂 | |
| DE60023146T2 (de) | Kondensierte indolinderivate und deren verwendung als 5ht-,insbesondere 5ht2c, rezeptorliganden | |
| DE19955794A1 (de) | Pyrrolidin-Derivate-CCR-3-Rezeptor-Antagonisten | |
| FR2741621A1 (fr) | Nouveaux derives de pyrazole, procede pour leur preparation et compositions pharmaceutiques en contenant | |
| DE60112059T2 (de) | Therapeutisch verwendbare diphenyletherverbindungen | |
| DE3712735A1 (de) | Neue pyrazolo(3,4-d)pyrimidine, verfahren zu ihrer herstellung und verwendung als arzneimittel | |
| WO2000012482A2 (en) | Indazole derivatives with 5-ht2 receptor activity | |
| SK2012003A3 (en) | Phenoxybenzylamine derivatives as selective re-uptake inhibitors | |
| DE69611728T2 (de) | N-(4-substituerte benzyl)-2-aminolactamderivate | |
| DE3542698A1 (de) | Indolderivate, verfahren zu ihrer herstellung und sie enthaltende, pharmazeutische zubereitungen | |
| WO2000017170A2 (en) | N1-substituted benzopyrazoles as inhibitors of 5-ht2 receptors | |
| DE602004004378T2 (de) | Verbindungen mit einer 5-ht2c rezeptor-wirkung und ihre verwendung | |
| DE3543982A1 (de) | Indolderivate, verfahren zu ihrer herstellung und sie enthaltende, pharmazeutische zubereitungen | |
| DE3309596A1 (de) | 2-substituierte 1-(3'-aminoalkyl)-1,2,3,4-tetrahydro-ss-carboline, ihre herstellung und verwendung als arzneimittel | |
| KR860001253B1 (ko) | 9-[3-(3, 5-시스-디메틸피페라지노)프로필] 카르바졸의 제조방법 | |
| DE69614407T2 (de) | Pharmazeutische zusammensetzungen | |
| DE69411589T2 (de) | Indol, indolin und chinolin derivate mit einer 5ht1d antagonistischen wirkung | |
| DE69703242T2 (de) | Indolin-derivate verwendbar als 5-ht-2c rezeptor-antagonisten |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |