IL181387A - Fused tricyclic derivatives for the treatment of psychotic disorders - Google Patents

Info

Publication number

IL181387A

IL181387A IL181387A IL18138707A IL181387A IL 181387 A IL181387 A IL 181387A IL 181387 A IL181387 A IL 181387A IL 18138707 A IL18138707 A IL 18138707A IL 181387 A IL181387 A IL 181387A

Authority

IL

Israel

Prior art keywords

disorder

methyl

mmol

6alkyl

ethyl

Prior art date

2004-08-31

Links

• Espacenet
• Global Dossier
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• 208000028017 Psychotic disease Diseases 0.000 title claims description 23
• 238000011282 treatment Methods 0.000 title description 26
• 150000001875 compounds Chemical class 0.000 claims description 458
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 133
• -1 cyano, nitro, amino Chemical group 0.000 claims description 74
• 229910052736 halogen Inorganic materials 0.000 claims description 66
• 229910052739 hydrogen Inorganic materials 0.000 claims description 62
• 239000001257 hydrogen Substances 0.000 claims description 52
• 239000012458 free base Substances 0.000 claims description 51
• 125000001424 substituent group Chemical group 0.000 claims description 51
• 150000002367 halogens Chemical class 0.000 claims description 50
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 49
• 125000003118 aryl group Chemical group 0.000 claims description 45
• 150000003839 salts Chemical class 0.000 claims description 45
• 229910052757 nitrogen Inorganic materials 0.000 claims description 44
• 125000000623 heterocyclic group Chemical group 0.000 claims description 39
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 34
• 150000002431 hydrogen Chemical group 0.000 claims description 34
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 34
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 32
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 29
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 26
• 229910052727 yttrium Inorganic materials 0.000 claims description 24
• 208000019901 Anxiety disease Diseases 0.000 claims description 22
• 125000003435 aroyl group Chemical group 0.000 claims description 21
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 21
• 208000019022 Mood disease Diseases 0.000 claims description 18
• 208000035475 disorder Diseases 0.000 claims description 18
• BLTDCIWCFCUQCB-UHFFFAOYSA-N quinoline-3-carboxamide Chemical compound C1=CC=CC2=CC(C(=O)N)=CN=C21 BLTDCIWCFCUQCB-UHFFFAOYSA-N 0.000 claims description 18
• 229910052760 oxygen Inorganic materials 0.000 claims description 17
• 239000002585 base Substances 0.000 claims description 16
• 206010026749 Mania Diseases 0.000 claims description 15
• 201000001880 Sexual dysfunction Diseases 0.000 claims description 14
• 201000010099 disease Diseases 0.000 claims description 14
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
• 231100000872 sexual dysfunction Toxicity 0.000 claims description 14
• 125000005843 halogen group Chemical group 0.000 claims description 13
• 125000004432 carbon atom Chemical group C* 0.000 claims description 12
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• 229910052717 sulfur Inorganic materials 0.000 claims description 11
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• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
• 125000005493 quinolyl group Chemical group 0.000 claims description 10
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• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 9
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• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
• 230000001404 mediated effect Effects 0.000 claims description 8
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
• 239000005864 Sulphur Chemical group 0.000 claims description 7
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
• 229910052799 carbon Inorganic materials 0.000 claims description 7
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
• 230000003001 depressive effect Effects 0.000 claims description 7
• 125000001072 heteroaryl group Chemical group 0.000 claims description 7
• 125000002883 imidazolyl group Chemical group 0.000 claims description 7
• 239000001301 oxygen Substances 0.000 claims description 7
• 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 6
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• 125000005724 cycloalkenylene group Chemical group 0.000 claims description 6
• 125000002993 cycloalkylene group Chemical group 0.000 claims description 6
• 125000001153 fluoro group Chemical group F* 0.000 claims description 6
• 239000008194 pharmaceutical composition Substances 0.000 claims description 6
• BTUQCUPQFZHMNS-UHFFFAOYSA-N quinoline;dihydrochloride Chemical compound Cl.Cl.N1=CC=CC2=CC=CC=C21 BTUQCUPQFZHMNS-UHFFFAOYSA-N 0.000 claims description 6
• 150000003536 tetrazoles Chemical class 0.000 claims description 6
• 150000003852 triazoles Chemical group 0.000 claims description 6
• QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims description 5
• NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 5
• 125000006413 ring segment Chemical group 0.000 claims description 5
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• 231100000395 Substance-induced mood disorder Toxicity 0.000 claims description 4
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
• 125000001041 indolyl group Chemical group 0.000 claims description 4
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• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
• HLQJZFFWUXHYMB-UHFFFAOYSA-N 6-[2-[4-(2-methylquinolin-5-yl)piperazin-1-yl]ethyl]-4h-imidazo[5,1-c][1,4]benzoxazine-3-carboxamide Chemical compound O1CC2=C(C(N)=O)N=CN2C2=C1C(CCN1CCN(CC1)C=1C3=CC=C(N=C3C=CC=1)C)=CC=C2 HLQJZFFWUXHYMB-UHFFFAOYSA-N 0.000 claims description 3
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 3
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• 208000021663 Female sexual arousal disease Diseases 0.000 claims description 3
• 206010017389 Frotteurism Diseases 0.000 claims description 3
• 208000011688 Generalised anxiety disease Diseases 0.000 claims description 3
• 208000004547 Hallucinations Diseases 0.000 claims description 3
• 206010024419 Libido decreased Diseases 0.000 claims description 3
• 208000030431 Male orgasmic disease Diseases 0.000 claims description 3
• 206010026864 Masochism Diseases 0.000 claims description 3
• 241001465754 Metazoa Species 0.000 claims description 3
• 206010027944 Mood disorder due to a general medical condition Diseases 0.000 claims description 3
• 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 3
• 206010033664 Panic attack Diseases 0.000 claims description 3
• 208000032769 Pedophilia Diseases 0.000 claims description 3
• 206010034912 Phobia Diseases 0.000 claims description 3
• 206010039367 Sadism Diseases 0.000 claims description 3
• 208000029901 Sexual arousal disease Diseases 0.000 claims description 3
• 208000029899 Sexual aversion disease Diseases 0.000 claims description 3
• 208000030047 Sexual desire disease Diseases 0.000 claims description 3
• 208000027520 Somatoform disease Diseases 0.000 claims description 3
• 208000011963 Substance-induced psychotic disease Diseases 0.000 claims description 3
• 231100000393 Substance-induced psychotic disorder Toxicity 0.000 claims description 3
• 208000031674 Traumatic Acute Stress disease Diseases 0.000 claims description 3
• 208000026345 acute stress disease Diseases 0.000 claims description 3
• 125000003545 alkoxy group Chemical group 0.000 claims description 3
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
• 208000028683 bipolar I disease Diseases 0.000 claims description 3
• 208000026725 cyclothymic disease Diseases 0.000 claims description 3
• 231100000868 delusion Toxicity 0.000 claims description 3
• 239000003085 diluting agent Substances 0.000 claims description 3
• 239000003937 drug carrier Substances 0.000 claims description 3
• 208000003481 exhibitionism Diseases 0.000 claims description 3
• 208000014840 female orgasmic disease Diseases 0.000 claims description 3
• 206010016531 fetishism Diseases 0.000 claims description 3
• 208000029364 generalized anxiety disease Diseases 0.000 claims description 3
• 125000005842 heteroatom Chemical group 0.000 claims description 3
• 208000017020 hypoactive sexual desire disease Diseases 0.000 claims description 3
• 201000004197 inhibited female orgasm Diseases 0.000 claims description 3
• 201000000068 inhibited male orgasm Diseases 0.000 claims description 3
• 208000015421 male orgasm disease Diseases 0.000 claims description 3
• 208000027753 pain disease Diseases 0.000 claims description 3
• 208000028173 post-traumatic stress disease Diseases 0.000 claims description 3
• 230000000306 recurrent effect Effects 0.000 claims description 3
• 201000000980 schizophrenia Diseases 0.000 claims description 3
• 208000012201 sexual and gender identity disease Diseases 0.000 claims description 3
• 208000015891 sexual disease Diseases 0.000 claims description 3
• 230000001568 sexual effect Effects 0.000 claims description 3
• 201000005814 sexual masochism Diseases 0.000 claims description 3
• 208000027599 sexual masochism disease Diseases 0.000 claims description 3
• 201000005841 sexual sadism Diseases 0.000 claims description 3
• 208000027596 sexual sadism disease Diseases 0.000 claims description 3
• 201000001716 specific phobia Diseases 0.000 claims description 3
• 201000005142 transvestism Diseases 0.000 claims description 3
• 206010046947 vaginismus Diseases 0.000 claims description 3
• 208000008918 voyeurism Diseases 0.000 claims description 3
• 206010002859 Anxiety disorder due to a general medical condition Diseases 0.000 claims description 2
• 208000021465 Brief psychotic disease Diseases 0.000 claims description 2
• 208000024254 Delusional disease Diseases 0.000 claims description 2
• 206010061921 Psychotic disorder due to a general medical condition Diseases 0.000 claims description 2
• 208000020186 Schizophreniform disease Diseases 0.000 claims description 2
• 208000019568 Shared Paranoid disease Diseases 0.000 claims description 2
• 208000028810 Shared psychotic disease Diseases 0.000 claims description 2
• 208000027418 Wounds and injury Diseases 0.000 claims description 2
• 125000000217 alkyl group Chemical group 0.000 claims description 2
• 208000022257 bipolar II disease Diseases 0.000 claims description 2
• 206010007776 catatonia Diseases 0.000 claims description 2
• 208000014674 injury Diseases 0.000 claims description 2
• 125000005647 linker group Chemical group 0.000 claims description 2
• 238000004519 manufacturing process Methods 0.000 claims description 2
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
• 208000002851 paranoid schizophrenia Diseases 0.000 claims description 2
• DJXNJVFEFSWHLY-UHFFFAOYSA-M quinoline-3-carboxylate Chemical compound C1=CC=CC2=CC(C(=O)[O-])=CN=C21 DJXNJVFEFSWHLY-UHFFFAOYSA-M 0.000 claims description 2
• 208000022610 schizoaffective disease Diseases 0.000 claims description 2
• 230000000392 somatic effect Effects 0.000 claims description 2
• 125000004434 sulfur atom Chemical group 0.000 claims description 2
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
• UKIVBICSZXPLKQ-UHFFFAOYSA-N 6-[2-[4-(2-methylquinolin-5-yl)piperidin-1-yl]ethyl]imidazo[1,5-a]quinoline-3-carboxamide Chemical compound C1=CC2=C(C(N)=O)N=CN2C2=C1C(CCN1CCC(CC1)C=1C3=CC=C(N=C3C=CC=1)C)=CC=C2 UKIVBICSZXPLKQ-UHFFFAOYSA-N 0.000 claims 1
• 150000005130 benzoxazines Chemical class 0.000 claims 1
• 230000002028 premature Effects 0.000 claims 1
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 426
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 329
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 329
• 239000000203 mixture Substances 0.000 description 210
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• 238000001819 mass spectrum Methods 0.000 description 198
• 238000005160 1H NMR spectroscopy Methods 0.000 description 178
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 168
• 239000007787 solid Substances 0.000 description 141
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 127
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 125
• 235000019439 ethyl acetate Nutrition 0.000 description 111
• 238000000034 method Methods 0.000 description 109
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• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 102
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 92
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• 239000000741 silica gel Substances 0.000 description 80
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• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 78
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 67
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 66
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• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 39
• 239000013058 crude material Substances 0.000 description 39
• 229960004132 diethyl ether Drugs 0.000 description 37
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
• 238000010992 reflux Methods 0.000 description 31
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 30
• JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 30
• 238000000746 purification Methods 0.000 description 29
• IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 27
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 26
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 26
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• 239000000047 product Substances 0.000 description 25
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• 238000004587 chromatography analysis Methods 0.000 description 24
• 229910000027 potassium carbonate Inorganic materials 0.000 description 22
• 229920006395 saturated elastomer Polymers 0.000 description 21
• 238000001665 trituration Methods 0.000 description 20
• 235000019441 ethanol Nutrition 0.000 description 19
• 239000003921 oil Substances 0.000 description 19
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• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 18
• 238000010640 amide synthesis reaction Methods 0.000 description 18
• 230000002829 reductive effect Effects 0.000 description 18
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 17
• 235000011114 ammonium hydroxide Nutrition 0.000 description 17
• 238000002360 preparation method Methods 0.000 description 17
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 16
• 239000007864 aqueous solution Substances 0.000 description 16
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 16
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 15
• 229960000583 acetic acid Drugs 0.000 description 15
• 238000004128 high performance liquid chromatography Methods 0.000 description 15
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• 238000005481 NMR spectroscopy Methods 0.000 description 14
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• 239000000543 intermediate Substances 0.000 description 14
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• 239000012321 sodium triacetoxyborohydride Substances 0.000 description 14
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• 238000001914 filtration Methods 0.000 description 13
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 12
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• YIBLESRXXRRDMB-UHFFFAOYSA-N 2-(1-methyl-4h-[1,2,4]triazolo[3,4-c][1,4]benzoxazin-6-yl)acetaldehyde Chemical compound C1=CC=C2N3C(C)=NN=C3COC2=C1CC=O YIBLESRXXRRDMB-UHFFFAOYSA-N 0.000 description 10
• PZNAAXFCMFHGNR-UHFFFAOYSA-N 2-methyl-5-piperazin-1-ylquinoline Chemical compound C=1C=CC2=NC(C)=CC=C2C=1N1CCNCC1 PZNAAXFCMFHGNR-UHFFFAOYSA-N 0.000 description 10
• HNQCTKVOLVBTCG-UHFFFAOYSA-N 8-prop-2-enyl-4h-1,4-benzoxazin-3-one Chemical compound N1C(=O)COC2=C1C=CC=C2CC=C HNQCTKVOLVBTCG-UHFFFAOYSA-N 0.000 description 10
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• ODKIQEITOADWNR-UHFFFAOYSA-M potassium;6-[2-[4-(2-methylquinolin-5-yl)piperazin-1-yl]ethyl]-4h-imidazo[5,1-c][1,4]benzoxazine-3-carboxylate Chemical compound [K+].O1CC2=C(C([O-])=O)N=CN2C2=C1C(CCN1CCN(CC1)C=1C3=CC=C(N=C3C=CC=1)C)=CC=C2 ODKIQEITOADWNR-UHFFFAOYSA-M 0.000 description 10
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 10
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• 239000000377 silicon dioxide Substances 0.000 description 9
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