NZ201740A - Tricyclic ethers and pharmaceutical compositions - Google Patents
Tricyclic ethers and pharmaceutical compositionsInfo
- Publication number
- NZ201740A NZ201740A NZ201740A NZ20174082A NZ201740A NZ 201740 A NZ201740 A NZ 201740A NZ 201740 A NZ201740 A NZ 201740A NZ 20174082 A NZ20174082 A NZ 20174082A NZ 201740 A NZ201740 A NZ 201740A
- Authority
- NZ
- New Zealand
- Prior art keywords
- general formula
- formula
- group
- derivative
- lower alkyl
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 6
- 150000002170 ethers Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 43
- -1 pyrrolidino, piperidino Chemical group 0.000 claims abstract description 28
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 claims abstract description 5
- 239000011707 mineral Substances 0.000 claims abstract description 5
- 150000003839 salts Chemical class 0.000 claims abstract description 5
- 125000002252 acyl group Chemical group 0.000 claims abstract description 4
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract description 4
- 150000007522 mineralic acids Chemical class 0.000 claims abstract description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 3
- 230000003287 optical effect Effects 0.000 claims abstract description 3
- 150000007524 organic acids Chemical class 0.000 claims abstract description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 14
- 239000003795 chemical substances by application Substances 0.000 claims description 13
- 150000002513 isocyanates Chemical class 0.000 claims description 12
- 230000008569 process Effects 0.000 claims description 12
- 150000002596 lactones Chemical class 0.000 claims description 11
- 230000009471 action Effects 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 9
- 150000004678 hydrides Chemical class 0.000 claims description 8
- 150000001540 azides Chemical class 0.000 claims description 7
- 238000005984 hydrogenation reaction Methods 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 6
- 239000012948 isocyanate Substances 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 4
- 150000002825 nitriles Chemical class 0.000 claims description 4
- ATYBXHSAIOKLMG-UHFFFAOYSA-N oxepin Chemical compound O1C=CC=CC=C1 ATYBXHSAIOKLMG-UHFFFAOYSA-N 0.000 claims description 4
- 238000007127 saponification reaction Methods 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 3
- 150000003947 ethylamines Chemical class 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 150000003512 tertiary amines Chemical class 0.000 claims description 3
- 238000006969 Curtius rearrangement reaction Methods 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical group ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- WDWDWGRYHDPSDS-UHFFFAOYSA-N methanimine Chemical compound N=C WDWDWGRYHDPSDS-UHFFFAOYSA-N 0.000 claims description 2
- 231100000252 nontoxic Toxicity 0.000 claims description 2
- 230000003000 nontoxic effect Effects 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 150000003141 primary amines Chemical class 0.000 claims description 2
- 150000003335 secondary amines Chemical class 0.000 claims description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims description 2
- 125000005079 alkoxycarbonylmethyl group Chemical group 0.000 claims 1
- 229940100198 alkylating agent Drugs 0.000 claims 1
- 239000002168 alkylating agent Substances 0.000 claims 1
- 150000008064 anhydrides Chemical class 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- VPKDCDLSJZCGKE-UHFFFAOYSA-N methanediimine Chemical compound N=C=N VPKDCDLSJZCGKE-UHFFFAOYSA-N 0.000 claims 1
- 150000003956 methylamines Chemical class 0.000 claims 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 claims 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical class CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims 1
- 239000000935 antidepressant agent Substances 0.000 abstract description 3
- 229940005513 antidepressants Drugs 0.000 abstract description 3
- 125000005843 halogen group Chemical group 0.000 abstract description 2
- 125000004193 piperazinyl group Chemical group 0.000 abstract 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 27
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- 239000000047 product Substances 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 7
- 241000699670 Mus sp. Species 0.000 description 7
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 241000700159 Rattus Species 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 238000007912 intraperitoneal administration Methods 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- WXLCDTBTIVJDCE-UHFFFAOYSA-N 1,4-oxazepine Chemical compound O1C=CC=NC=C1 WXLCDTBTIVJDCE-UHFFFAOYSA-N 0.000 description 3
- KDTQBESFYGHFDV-UHFFFAOYSA-N 4aH-benzo[c]chromene Chemical compound C1=CC=CC2OC=C(C=CC=C3)C3=C21 KDTQBESFYGHFDV-UHFFFAOYSA-N 0.000 description 3
- 206010001488 Aggression Diseases 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- 238000005406 washing Methods 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
- MKJIEFSOBYUXJB-HOCLYGCPSA-N (3S,11bS)-9,10-dimethoxy-3-isobutyl-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one Chemical compound C1CN2C[C@H](CC(C)C)C(=O)C[C@H]2C2=C1C=C(OC)C(OC)=C2 MKJIEFSOBYUXJB-HOCLYGCPSA-N 0.000 description 2
- MCBZDKLONLHDTJ-UHFFFAOYSA-N 1-(6H-benzo[c][1,5]benzoxazepin-11-yl)ethanone Chemical compound C1OC2=CC=CC=C2N(C(=O)C)C2=CC=CC=C21 MCBZDKLONLHDTJ-UHFFFAOYSA-N 0.000 description 2
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- VKLACUMOQISWBI-UHFFFAOYSA-N C1=CC2C(=C3C=CC=CC3=C(O2)CCO)C=C1 Chemical compound C1=CC2C(=C3C=CC=CC3=C(O2)CCO)C=C1 VKLACUMOQISWBI-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 230000000949 anxiolytic effect Effects 0.000 description 2
- 230000006399 behavior Effects 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 230000002631 hypothermal effect Effects 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- NTNUDYROPUKXNA-UHFFFAOYSA-N methyl 2-(triphenyl-$l^{5}-phosphanylidene)acetate Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC(=O)OC)C1=CC=CC=C1 NTNUDYROPUKXNA-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000000926 neurological effect Effects 0.000 description 2
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 229910003446 platinum oxide Inorganic materials 0.000 description 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 229960005333 tetrabenazine Drugs 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 2
- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 1
- NGEXZCPRUNDMRB-UHFFFAOYSA-N 1-hydroxy-2-phenylcyclohexa-2,4-diene-1-carboxylic acid Chemical group OC1(C(=CC=CC1)C1=CC=CC=C1)C(=O)O NGEXZCPRUNDMRB-UHFFFAOYSA-N 0.000 description 1
- QSAPSMINSSXSRH-UHFFFAOYSA-N 11-methyl-6H-benzo[c][1,5]benzoxazepine Chemical compound C1OC2=CC=CC=C2N(C)C2=CC=CC=C21 QSAPSMINSSXSRH-UHFFFAOYSA-N 0.000 description 1
- IPDWABJNXLNLRA-UHFFFAOYSA-N 2,3-dihydroxybutanedioic acid;2-hydroxypropane-1,2,3-tricarboxylic acid Chemical compound OC(=O)C(O)C(O)C(O)=O.OC(=O)CC(O)(C(O)=O)CC(O)=O IPDWABJNXLNLRA-UHFFFAOYSA-N 0.000 description 1
- SPXRGBRACNDQPA-UHFFFAOYSA-N 2-phosphanylacetonitrile Chemical compound PCC#N SPXRGBRACNDQPA-UHFFFAOYSA-N 0.000 description 1
- KSCDZOHRENNCGF-UHFFFAOYSA-N 3-(4aH-benzo[c]chromen-6-yl)propan-1-amine Chemical compound NCCCC1=C2C(=C3C(O1)C=CC=C3)C=CC=C2 KSCDZOHRENNCGF-UHFFFAOYSA-N 0.000 description 1
- FPIWJQQRYHEICX-UHFFFAOYSA-N 6,11-dihydrobenzo[c][1]benzoxepine Chemical class C1OC2=CC=CC=C2CC2=CC=CC=C12 FPIWJQQRYHEICX-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- WKDDNLLKINBNMK-UHFFFAOYSA-N C1=CC2C(=C3C=CC=CC3=C(O2)CCC#N)C=C1 Chemical compound C1=CC2C(=C3C=CC=CC3=C(O2)CCC#N)C=C1 WKDDNLLKINBNMK-UHFFFAOYSA-N 0.000 description 1
- PGJVGAAVGIRCKH-UHFFFAOYSA-N C1=CC=C2C(=C1)C(=O)N(C2=O)CC3=C4C=CC=CC4=C5C=CC=CC5O3 Chemical compound C1=CC=C2C(=C1)C(=O)N(C2=O)CC3=C4C=CC=CC4=C5C=CC=CC5O3 PGJVGAAVGIRCKH-UHFFFAOYSA-N 0.000 description 1
- KZQDKDRMSDVWEY-UHFFFAOYSA-N C1=CC=CC=C1[PH2](C=1C=CC=CC=1)C1=CC=CC=C1 Chemical compound C1=CC=CC=C1[PH2](C=1C=CC=CC=1)C1=CC=CC=C1 KZQDKDRMSDVWEY-UHFFFAOYSA-N 0.000 description 1
- 241000518994 Conta Species 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- 101000830713 Homo sapiens Torsin-3A Proteins 0.000 description 1
- 101000618467 Hypocrea jecorina (strain ATCC 56765 / BCRC 32924 / NRRL 11460 / Rut C-30) Endo-1,4-beta-xylanase 2 Proteins 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
- UEQUQVLFIPOEMF-UHFFFAOYSA-N Mianserin Chemical compound C1C2=CC=CC=C2N2CCN(C)CC2C2=CC=CC=C21 UEQUQVLFIPOEMF-UHFFFAOYSA-N 0.000 description 1
- 208000019695 Migraine disease Diseases 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 1
- QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 102100024603 Torsin-3A Human genes 0.000 description 1
- 238000002679 ablation Methods 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
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- 230000008485 antagonism Effects 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 239000002249 anxiolytic agent Substances 0.000 description 1
- VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 description 1
- 229960004046 apomorphine Drugs 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
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- 229940125773 compound 10 Drugs 0.000 description 1
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- 210000000744 eyelid Anatomy 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 208000013403 hyperactivity Diseases 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000155 melt Chemical class 0.000 description 1
- QUZHETYGXCOZJV-UHFFFAOYSA-N methyl 2-benzo[c][1]benzoxepin-6-ylacetate Chemical compound O1C(CC(=O)OC)=C2C=CC=CC2=CC2=CC=CC=C21 QUZHETYGXCOZJV-UHFFFAOYSA-N 0.000 description 1
- KQACHGKROWTUPZ-UHFFFAOYSA-N methyl 2-benzo[c]chromen-6-ylideneacetate Chemical compound COC(=O)C=C1C2=C(C3=C(O1)C=CC=C3)C=CC=C2 KQACHGKROWTUPZ-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 229960003955 mianserin Drugs 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 206010027599 migraine Diseases 0.000 description 1
- 230000002969 morbid Effects 0.000 description 1
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- 235000006408 oxalic acid Nutrition 0.000 description 1
- BAAJAGGOVDGDSI-UHFFFAOYSA-N oxepin-3-one Chemical compound O=C1COC=CC=C1 BAAJAGGOVDGDSI-UHFFFAOYSA-N 0.000 description 1
- 150000004880 oxines Chemical class 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 230000000506 psychotropic effect Effects 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 1
- 229960003147 reserpine Drugs 0.000 description 1
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000009291 secondary effect Effects 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D313/00—Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom
- C07D313/02—Seven-membered rings
- C07D313/06—Seven-membered rings condensed with carbocyclic rings or ring systems
- C07D313/10—Seven-membered rings condensed with carbocyclic rings or ring systems condensed with two six-membered rings
- C07D313/12—[b,e]-condensed
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D267/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D267/02—Seven-membered rings
- C07D267/08—Seven-membered rings having the hetero atoms in positions 1 and 4
- C07D267/12—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D267/16—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems condensed with two six-membered rings
- C07D267/18—[b, e]-condensed
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Anesthesiology (AREA)
- Animal Behavior & Ethology (AREA)
- Biomedical Technology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Hydrogenated Pyridines (AREA)
- Pyrane Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Luminescent Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8116347A FR2512024A1 (fr) | 1981-08-27 | 1981-08-27 | Ethers tricycliques, leur preparation et les compositions pharmaceutiques les contenant |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ201740A true NZ201740A (en) | 1985-05-31 |
Family
ID=9261704
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ201740A NZ201740A (en) | 1981-08-27 | 1982-08-27 | Tricyclic ethers and pharmaceutical compositions |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4496557A (oth) |
| EP (1) | EP0074304B1 (oth) |
| JP (1) | JPS5874673A (oth) |
| AT (1) | ATE12497T1 (oth) |
| AU (1) | AU8773082A (oth) |
| CA (1) | CA1227481A (oth) |
| DE (1) | DE3262880D1 (oth) |
| ES (1) | ES515232A0 (oth) |
| FR (1) | FR2512024A1 (oth) |
| GR (1) | GR77595B (oth) |
| IL (1) | IL66650A (oth) |
| NZ (1) | NZ201740A (oth) |
| PT (1) | PT75471B (oth) |
| ZA (1) | ZA826252B (oth) |
Families Citing this family (70)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE8500273D0 (sv) * | 1985-01-22 | 1985-01-22 | Leo Ab | Nya tricykliska foreningar, kompositioner innehallande sadana foreningar, framstellningsforfaranden och behandlingsmetoder |
| EP0332246A1 (en) * | 1988-03-11 | 1989-09-13 | Akzo N.V. | Tricyclic amine derivatives |
| US5180736A (en) * | 1989-03-23 | 1993-01-19 | Warner-Lambert Company | Polycyclic amines useful as cerebrovascular agents |
| US5260319A (en) * | 1989-12-26 | 1993-11-09 | Hoechst-Roussel Pharmaceuticals Incorporated | Thienobenzoxepins and naphthothiophenes |
| US5006536A (en) * | 1989-12-26 | 1991-04-09 | Hoechst-Roussel Pharmaceuticals Inc. | Thienobenzoxepins and analgesic compositions thereof |
| US5574173A (en) * | 1993-12-06 | 1996-11-12 | Schering Corporation | Tricyclic derivatives, compositions and methods of use |
| PT726265E (pt) * | 1995-02-08 | 2001-12-28 | Novartis Ag | 10-amino-alifatil-dibenzo¬b,f| oxepinas com accao antineurodegenerativa |
| US5698551A (en) * | 1995-04-07 | 1997-12-16 | Novo Nordisk A/S | Heterocyclic compounds |
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| US7662082B2 (en) | 2004-11-05 | 2010-02-16 | Theragenics Corporation | Expandable brachytherapy device |
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| US7630533B2 (en) | 2007-09-20 | 2009-12-08 | Hologic, Inc. | Breast tomosynthesis with display of highlighted suspected calcifications |
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| EP3311748A3 (en) | 2008-09-04 | 2018-05-09 | Hologic Inc. | Integrated multi-mode mammography/tomosynthesis x-ray system |
| US9248311B2 (en) | 2009-02-11 | 2016-02-02 | Hologic, Inc. | System and method for modifying a flexibility of a brachythereapy catheter |
| US9579524B2 (en) | 2009-02-11 | 2017-02-28 | Hologic, Inc. | Flexible multi-lumen brachytherapy device |
| US8170320B2 (en) * | 2009-03-03 | 2012-05-01 | Hologic, Inc. | Mammography/tomosynthesis systems and methods automatically deriving breast characteristics from breast x-ray images and automatically adjusting image processing parameters accordingly |
| US10207126B2 (en) | 2009-05-11 | 2019-02-19 | Cytyc Corporation | Lumen visualization and identification system for multi-lumen balloon catheter |
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| US9352172B2 (en) | 2010-09-30 | 2016-05-31 | Hologic, Inc. | Using a guide member to facilitate brachytherapy device swap |
| KR101836549B1 (ko) | 2010-10-05 | 2018-03-08 | 홀로직, 인크. | Ｃｔ 모드, 다중 단층영상합성 모드들, 및 유방조영술 모드를 갖는 직립형 ｘ-레이 유방 촬영 |
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| JP6392309B2 (ja) | 2013-03-15 | 2018-09-19 | ホロジック インコーポレイティッド | 自動合焦を含む、トモシンセシススタックをナビゲートするためのシステム |
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| US12414217B2 (en) | 2022-02-07 | 2025-09-09 | Hologic, Inc. | Systems and methods for adaptively controlling filament current in an X-ray tube |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3609167A (en) * | 1962-04-02 | 1971-09-28 | Smith Kline French Lab | IBENZO{8 b,e{9 {0 THIEPINES |
| NL125253C (oth) * | 1963-12-05 | |||
| NL152845B (nl) * | 1966-03-11 | 1977-04-15 | Boehringer Mannheim Gmbh | Werkwijze voor het bereiden van een geneesmiddel met een psychotrope en bloedsomloopstimulerende werking, alsmede het aldus verkregen gevormde geneesmiddel, en werkwijze voor het bereiden van een geneeskrachtig omega,omega-difenylalkylaminederivaat. |
| FR1518226A (fr) * | 1966-04-09 | 1968-03-22 | Boehringer & Soehne Gmbh | Procédé pour la préparation de dérivés tricy cliques n-alcoylés de l'acétamide |
| US4463001A (en) * | 1980-10-20 | 1984-07-31 | Farmitalia Carlo Erba S.P.A. | 6-Substituted 6H-dibenzo[b,d]pyran derivatives and process for their preparation |
-
1981
- 1981-08-27 FR FR8116347A patent/FR2512024A1/fr active Granted
-
1982
- 1982-08-16 US US06/408,451 patent/US4496557A/en not_active Expired - Fee Related
- 1982-08-20 CA CA000409886A patent/CA1227481A/fr not_active Expired
- 1982-08-24 AT AT82401567T patent/ATE12497T1/de active
- 1982-08-24 EP EP82401567A patent/EP0074304B1/fr not_active Expired
- 1982-08-24 DE DE8282401567T patent/DE3262880D1/de not_active Expired
- 1982-08-25 ES ES515232A patent/ES515232A0/es active Granted
- 1982-08-25 GR GR69103A patent/GR77595B/el unknown
- 1982-08-26 JP JP57148452A patent/JPS5874673A/ja active Granted
- 1982-08-26 PT PT75471A patent/PT75471B/pt unknown
- 1982-08-26 AU AU87730/82A patent/AU8773082A/en not_active Abandoned
- 1982-08-26 IL IL66650A patent/IL66650A/xx unknown
- 1982-08-26 ZA ZA826252A patent/ZA826252B/xx unknown
- 1982-08-27 NZ NZ201740A patent/NZ201740A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ATE12497T1 (de) | 1985-04-15 |
| FR2512024A1 (fr) | 1983-03-04 |
| DE3262880D1 (en) | 1985-05-09 |
| IL66650A (en) | 1985-08-30 |
| IL66650A0 (en) | 1982-12-31 |
| AU8773082A (en) | 1983-03-03 |
| ES8400422A1 (es) | 1983-11-01 |
| PT75471A (fr) | 1982-09-01 |
| ZA826252B (en) | 1983-07-27 |
| JPS6129950B2 (oth) | 1986-07-10 |
| EP0074304A1 (fr) | 1983-03-16 |
| CA1227481A (fr) | 1987-09-29 |
| GR77595B (oth) | 1984-09-25 |
| ES515232A0 (es) | 1983-11-01 |
| FR2512024B1 (oth) | 1984-01-06 |
| JPS5874673A (ja) | 1983-05-06 |
| EP0074304B1 (fr) | 1985-04-03 |
| US4496557A (en) | 1985-01-29 |
| PT75471B (fr) | 1984-11-19 |
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