IL45130A - Aminodibenzo (b,d) pyrans - Google Patents
Aminodibenzo (b,d) pyransInfo
- Publication number
- IL45130A IL45130A IL45130A IL4513074A IL45130A IL 45130 A IL45130 A IL 45130A IL 45130 A IL45130 A IL 45130A IL 4513074 A IL4513074 A IL 4513074A IL 45130 A IL45130 A IL 45130A
- Authority
- IL
- Israel
- Prior art keywords
- dibenzo
- pyran
- trimethyl
- tetrahydro
- amino
- Prior art date
Links
- 150000004880 oxines Chemical class 0.000 title abstract description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 81
- -1 alkali metal salt Chemical class 0.000 claims description 58
- 150000001875 compounds Chemical class 0.000 claims description 57
- 238000000034 method Methods 0.000 claims description 38
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
- KDTQBESFYGHFDV-UHFFFAOYSA-N 4aH-benzo[c]chromene Chemical class C1=CC=CC2OC=C(C=CC=C3)C3=C21 KDTQBESFYGHFDV-UHFFFAOYSA-N 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- 229910052783 alkali metal Inorganic materials 0.000 claims description 9
- 239000012442 inert solvent Substances 0.000 claims description 9
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 claims description 8
- OBHKONRNYCDRKM-UHFFFAOYSA-N 4-chloro-2-phenylquinazoline Chemical compound N=1C2=CC=CC=C2C(Cl)=NC=1C1=CC=CC=C1 OBHKONRNYCDRKM-UHFFFAOYSA-N 0.000 claims description 8
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 8
- 239000003513 alkali Substances 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 7
- 125000003282 alkyl amino group Chemical group 0.000 claims description 7
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 5
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 5
- 239000012312 sodium hydride Substances 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- SGNBEQXWGWKCBH-UHFFFAOYSA-N COC(CO[AlH2])OC.[Na] Chemical compound COC(CO[AlH2])OC.[Na] SGNBEQXWGWKCBH-UHFFFAOYSA-N 0.000 claims description 4
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims description 4
- 239000012346 acetyl chloride Substances 0.000 claims description 4
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 4
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 3
- 150000001266 acyl halides Chemical class 0.000 claims description 2
- 229910000102 alkali metal hydride Inorganic materials 0.000 claims description 2
- 150000008046 alkali metal hydrides Chemical class 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 150000004678 hydrides Chemical class 0.000 claims description 2
- 230000002152 alkylating effect Effects 0.000 claims 2
- SGGWYTSWKPDCSZ-UHFFFAOYSA-N 6,6,9-trimethyl-3-pentyl-7,8,9,10-tetrahydrobenzo[c]chromen-1-amine Chemical compound CC1(C)OC2=CC(CCCCC)=CC(N)=C2C2=C1CCC(C)C2 SGGWYTSWKPDCSZ-UHFFFAOYSA-N 0.000 claims 1
- LEERCLQAIDHVTC-UHFFFAOYSA-N 6,6,9-trimethylbenzo[c]chromene Chemical compound CC1(C2=C(C3=C(O1)C=CC=C3)C=C(C=C2)C)C LEERCLQAIDHVTC-UHFFFAOYSA-N 0.000 claims 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 claims 1
- 238000005932 reductive alkylation reaction Methods 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 230000001430 anti-depressive effect Effects 0.000 abstract description 3
- 239000000935 antidepressant agent Substances 0.000 abstract description 3
- 239000000730 antalgic agent Substances 0.000 abstract description 2
- 230000000049 anti-anxiety effect Effects 0.000 abstract description 2
- 239000002249 anxiolytic agent Substances 0.000 abstract description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- 150000001793 charged compounds Chemical class 0.000 description 22
- 238000010521 absorption reaction Methods 0.000 description 21
- 108700039708 galantide Proteins 0.000 description 19
- 239000000126 substance Substances 0.000 description 14
- 101150041968 CDC13 gene Proteins 0.000 description 13
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 13
- 125000003118 aryl group Chemical group 0.000 description 11
- 238000001704 evaporation Methods 0.000 description 10
- 230000008020 evaporation Effects 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 244000025254 Cannabis sativa Species 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 7
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 229960004242 dronabinol Drugs 0.000 description 6
- 229940079593 drug Drugs 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 5
- XYHKNCXZYYTLRG-UHFFFAOYSA-N 1h-imidazole-2-carbaldehyde Chemical compound O=CC1=NC=CN1 XYHKNCXZYYTLRG-UHFFFAOYSA-N 0.000 description 4
- ZPSJGADGUYYRKE-UHFFFAOYSA-N 2H-pyran-2-one Chemical class O=C1C=CC=CO1 ZPSJGADGUYYRKE-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 230000000202 analgesic effect Effects 0.000 description 4
- OTAFHZMPRISVEM-UHFFFAOYSA-N chromone Chemical compound C1=CC=C2C(=O)C=COC2=C1 OTAFHZMPRISVEM-UHFFFAOYSA-N 0.000 description 4
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 4
- 239000012259 ether extract Substances 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 238000004809 thin layer chromatography Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000004866 Hashish Substances 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 3
- 230000003470 muricidal effect Effects 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- VOLMSPGWNYJHQQ-UHFFFAOYSA-N Pyranone Natural products CC1=C(O)C(=O)C(O)CO1 VOLMSPGWNYJHQQ-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- CYQFCXCEBYINGO-UHFFFAOYSA-N THC Natural products C1=C(C)CCC2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3C21 CYQFCXCEBYINGO-UHFFFAOYSA-N 0.000 description 2
- JEDZLBFUGJTJGQ-UHFFFAOYSA-N [Na].COCCO[AlH]OCCOC Chemical compound [Na].COCCO[AlH]OCCOC JEDZLBFUGJTJGQ-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 239000002830 appetite depressant Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- CYQFCXCEBYINGO-IAGOWNOFSA-N delta1-THC Chemical compound C1=C(C)CC[C@H]2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3[C@@H]21 CYQFCXCEBYINGO-IAGOWNOFSA-N 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 229940093476 ethylene glycol Drugs 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000007903 gelatin capsule Substances 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([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
- 230000003287 optical effect Effects 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 238000012552 review Methods 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 238000007920 subcutaneous administration Methods 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- HTNVFUBCWIYPJN-HSZRJFAPSA-N (3r)-3,5-dimethyl-3-(4-methylpent-3-enyl)-11h-pyrano[3,2-a]carbazole Chemical compound C1=CC=C2C3=CC(C)=C4O[C@@](CCC=C(C)C)(C)C=CC4=C3NC2=C1 HTNVFUBCWIYPJN-HSZRJFAPSA-N 0.000 description 1
- NEAOBZHAFUAIBY-UHFFFAOYSA-N 1-methyl-6h-benzo[c]chromene Chemical compound O1CC2=CC=CC=C2C2=C1C=CC=C2C NEAOBZHAFUAIBY-UHFFFAOYSA-N 0.000 description 1
- 125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004917 3-methyl-2-butyl group Chemical group CC(C(C)*)C 0.000 description 1
- 125000004919 3-methyl-2-pentyl group Chemical group CC(C(C)*)CC 0.000 description 1
- IYSNKBSTNGTBSO-UHFFFAOYSA-N 6,6,9-trimethyl-7,8,9,10-tetrahydrobenzo[c]chromene Chemical compound C12=CC=CC=C2OC(C)(C)C2=C1CC(C)CC2 IYSNKBSTNGTBSO-UHFFFAOYSA-N 0.000 description 1
- RZBKYXXDBLRMSI-UHFFFAOYSA-N CC(C(CCCCC)C)C=1C=C(C2=C(OCC3=C2CC(CC3)C)C1)O Chemical compound CC(C(CCCCC)C)C=1C=C(C2=C(OCC3=C2CC(CC3)C)C1)O RZBKYXXDBLRMSI-UHFFFAOYSA-N 0.000 description 1
- 241000218236 Cannabis Species 0.000 description 1
- 235000008697 Cannabis sativa Nutrition 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- 229930194542 Keto Natural products 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 229940125713 antianxiety drug Drugs 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 1
- ASIPLGLDOUQLOQ-UHFFFAOYSA-N benzo[c]chromen-1-one Chemical compound C1=CC=CC2=C3C(=O)C=CC=C3OC=C21 ASIPLGLDOUQLOQ-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001589 carboacyl group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- UOCJDOLVGGIYIQ-PBFPGSCMSA-N cefatrizine Chemical group S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)[C@H](N)C=2C=CC(O)=CC=2)CC=1CSC=1C=NNN=1 UOCJDOLVGGIYIQ-PBFPGSCMSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 206010013663 drug dependence Diseases 0.000 description 1
- FGSGHBPKHFDJOP-UHFFFAOYSA-N ethyl 2-oxocyclohexane-1-carboxylate Chemical compound CCOC(=O)C1CCCCC1=O FGSGHBPKHFDJOP-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 230000022244 formylation Effects 0.000 description 1
- 238000006170 formylation reaction Methods 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 230000008775 paternal effect Effects 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000012261 resinous substance Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 208000011117 substance-related disease Diseases 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229940066768 systemic antihistamines aminoalkyl ethers Drugs 0.000 description 1
- 229940125725 tranquilizer Drugs 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
- 229940086542 triethylamine Drugs 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- A61P25/24—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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Neurosurgery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Anesthesiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrane Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US385367A US3886184A (en) | 1973-08-03 | 1973-08-03 | Aminodibenzo(b,d)pyrans |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL45130A0 IL45130A0 (en) | 1974-09-10 |
| IL45130A true IL45130A (en) | 1977-10-31 |
Family
ID=23521121
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL45130A IL45130A (en) | 1973-08-03 | 1974-06-27 | Aminodibenzo (b,d) pyrans |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US3886184A (de) |
| JP (1) | JPS6011037B2 (de) |
| AR (2) | AR202030A1 (de) |
| AT (1) | AT336608B (de) |
| BE (1) | BE818418A (de) |
| BG (1) | BG22829A3 (de) |
| CA (1) | CA1023754A (de) |
| CH (1) | CH605893A5 (de) |
| DD (1) | DD112999A5 (de) |
| DE (1) | DE2437135C2 (de) |
| DK (1) | DK413074A (de) |
| ES (1) | ES428915A1 (de) |
| FR (1) | FR2240003B1 (de) |
| GB (1) | GB1481222A (de) |
| HU (1) | HU168622B (de) |
| IE (1) | IE39555B1 (de) |
| IL (1) | IL45130A (de) |
| NL (1) | NL7410351A (de) |
| PH (1) | PH10463A (de) |
| PL (1) | PL99837B1 (de) |
| SE (1) | SE7409999L (de) |
| SU (1) | SU555855A3 (de) |
| ZA (1) | ZA744095B (de) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4235913A (en) * | 1977-06-07 | 1980-11-25 | Pfizer Inc. | 9-Hydroxyhexahydrodibeno[b,d]pyrans, 1-substituted-9-hydroxyhexahydrodibenzo]b,d]pyrans |
| US4195025A (en) * | 1978-02-17 | 1980-03-25 | Eli Lilly And Company | 9-Amino-dibenzopyrans |
| US4454144A (en) * | 1982-06-21 | 1984-06-12 | Pfizer Inc. | Substituted dibenzo[b,d]pyran analgesics |
| US5264373A (en) * | 1987-02-17 | 1993-11-23 | Abbott Laboratories | Fluorescence polarization immunoassay for tetrahydrocannabinoids |
| US4931221A (en) * | 1988-12-30 | 1990-06-05 | Ppg Industries, Inc. | Photochromic spiropyran compounds |
| US5180736A (en) * | 1989-03-23 | 1993-01-19 | Warner-Lambert Company | Polycyclic amines useful as cerebrovascular agents |
| US5498419A (en) * | 1994-06-03 | 1996-03-12 | Pars; Harry G. | Fumarate salt of 4-(diethyl-3-(1-methyloctyl)-7,8,9,10-tetrahydro-6,6,9-trimethyl-6H-dibenzo[b,d]pyran-1-ol, 4-(diethyl-amino) butyric |
| CA2340445A1 (en) * | 1998-05-04 | 1999-11-11 | The University Of Connecticut | Novel analgesic and immunomodulatory cannabinoids |
| CA2340444A1 (en) * | 1998-05-04 | 1999-11-11 | The University Of Connecticut | Cannabinoids selective for the cb2 receptor |
| US7897598B2 (en) * | 1998-06-09 | 2011-03-01 | Alexandros Makriyannis | Inhibitors of the anandamide transporter |
| US7589220B2 (en) * | 1998-06-09 | 2009-09-15 | University Of Connecticut | Inhibitors of the anandamide transporter |
| US7161016B1 (en) | 1998-11-24 | 2007-01-09 | University Of Connecticut | Cannabimimetic lipid amides as useful medications |
| US7276613B1 (en) | 1998-11-24 | 2007-10-02 | University Of Connecticut | Retro-anandamides, high affinity and stability cannabinoid receptor ligands |
| US7393842B2 (en) * | 2001-08-31 | 2008-07-01 | University Of Connecticut | Pyrazole analogs acting on cannabinoid receptors |
| EP1223808B1 (de) | 1999-10-18 | 2007-03-07 | The University Of Connecticut | Für periphäre cannabinoid-rezeptoren selektive liganden |
| US8084467B2 (en) * | 1999-10-18 | 2011-12-27 | University Of Connecticut | Pyrazole derivatives as cannabinoid receptor antagonists |
| US7119108B1 (en) * | 1999-10-18 | 2006-10-10 | University Of Connecticut | Pyrazole derivatives as cannabinoid receptor antagonists |
| US7741365B2 (en) * | 1999-10-18 | 2010-06-22 | University Of Connecticut | Peripheral cannabinoid receptor (CB2) selective ligands |
| US6943266B1 (en) * | 1999-10-18 | 2005-09-13 | University Of Connecticut | Bicyclic cannabinoid agonists for the cannabinoid receptor |
| US6900236B1 (en) * | 1999-10-18 | 2005-05-31 | University Of Connecticut | Cannabimimetic indole derivatives |
| JP2004532185A (ja) * | 2001-01-26 | 2004-10-21 | ユニバーシティ オブ コネチカット | 新規なカンナビミメティックリガンド |
| ATE478670T1 (de) | 2001-01-29 | 2010-09-15 | Univ Connecticut | Rezeptor-selektive cannabimimetische aminoalkylindole |
| JP4312594B2 (ja) * | 2001-07-13 | 2009-08-12 | ユニバーシティ オブ コネチカット | 新規な二環式及び三環式カンナビノイド |
| CA2464333C (en) * | 2001-10-26 | 2011-07-26 | University Of Connecticut | Heteroindanes: a new class of potent cannabimimetic ligands |
| JP2006511460A (ja) | 2002-08-23 | 2006-04-06 | ユニバーシティ オブ コネチカット | 治療適応を持つケトカンナビノイド |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3656906A (en) * | 1970-04-13 | 1972-04-18 | Little Inc A | Method for detecting and quantitating the presence of cannabinoids and analogs thereof in biological materials and resulting products |
-
1973
- 1973-08-03 US US385367A patent/US3886184A/en not_active Expired - Lifetime
-
1974
- 1974-06-24 IE IE1327/74A patent/IE39555B1/xx unknown
- 1974-06-25 ZA ZA00744095A patent/ZA744095B/xx unknown
- 1974-06-27 IL IL45130A patent/IL45130A/en unknown
- 1974-06-28 CA CA203,730A patent/CA1023754A/en not_active Expired
- 1974-07-05 PH PH16017A patent/PH10463A/en unknown
- 1974-07-15 AR AR254694A patent/AR202030A1/es active
- 1974-07-30 PL PL1974173119A patent/PL99837B1/pl unknown
- 1974-08-01 AT AT633274A patent/AT336608B/de not_active IP Right Cessation
- 1974-08-01 DE DE2437135A patent/DE2437135C2/de not_active Expired
- 1974-08-01 NL NL7410351A patent/NL7410351A/xx not_active Application Discontinuation
- 1974-08-02 FR FR7427014A patent/FR2240003B1/fr not_active Expired
- 1974-08-02 CH CH1066674A patent/CH605893A5/xx not_active IP Right Cessation
- 1974-08-02 SE SE7409999A patent/SE7409999L/xx unknown
- 1974-08-02 GB GB34135/74A patent/GB1481222A/en not_active Expired
- 1974-08-02 BE BE1006106A patent/BE818418A/xx not_active IP Right Cessation
- 1974-08-02 ES ES428915A patent/ES428915A1/es not_active Expired
- 1974-08-02 SU SU2056163A patent/SU555855A3/ru active
- 1974-08-02 HU HUEI558A patent/HU168622B/hu unknown
- 1974-08-02 DD DD180291A patent/DD112999A5/xx unknown
- 1974-08-02 DK DK413074A patent/DK413074A/da unknown
- 1974-08-03 JP JP49089398A patent/JPS6011037B2/ja not_active Expired
- 1974-08-03 BG BG027424A patent/BG22829A3/xx unknown
-
1975
- 1975-04-21 AR AR258443A patent/AR202509A1/es active
Also Published As
| Publication number | Publication date |
|---|---|
| BE818418A (fr) | 1975-02-03 |
| BG22829A3 (bg) | 1977-04-20 |
| DE2437135A1 (de) | 1975-02-13 |
| SE7409999L (de) | 1975-02-04 |
| JPS5041866A (de) | 1975-04-16 |
| ZA744095B (en) | 1976-02-25 |
| DD112999A5 (de) | 1975-05-12 |
| PL99837B1 (pl) | 1978-08-31 |
| AT336608B (de) | 1977-05-10 |
| AR202030A1 (es) | 1975-05-09 |
| ATA633274A (de) | 1976-09-15 |
| NL7410351A (nl) | 1975-02-05 |
| FR2240003A1 (de) | 1975-03-07 |
| US3886184A (en) | 1975-05-27 |
| JPS6011037B2 (ja) | 1985-03-22 |
| AR202509A1 (es) | 1975-06-13 |
| DE2437135C2 (de) | 1983-12-29 |
| FR2240003B1 (de) | 1978-07-21 |
| DK413074A (de) | 1975-04-01 |
| HU168622B (de) | 1976-06-28 |
| IE39555L (en) | 1975-02-03 |
| CA1023754A (en) | 1978-01-03 |
| CH605893A5 (de) | 1978-10-13 |
| IE39555B1 (en) | 1978-11-08 |
| GB1481222A (en) | 1977-07-27 |
| ES428915A1 (es) | 1976-08-16 |
| PH10463A (en) | 1977-04-25 |
| AU7105574A (en) | 1976-01-15 |
| IL45130A0 (en) | 1974-09-10 |
| SU555855A3 (ru) | 1977-04-25 |
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