CA1063026A - Pharmaceutical preparation for hypnotics - Google Patents
Pharmaceutical preparation for hypnoticsInfo
- Publication number
- CA1063026A CA1063026A CA242,911A CA242911A CA1063026A CA 1063026 A CA1063026 A CA 1063026A CA 242911 A CA242911 A CA 242911A CA 1063026 A CA1063026 A CA 1063026A
- Authority
- CA
- Canada
- Prior art keywords
- propanol
- isopropylamino
- phenoxy
- pharmaceutical preparation
- salt
- 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
Links
- 239000003326 hypnotic agent Substances 0.000 title claims abstract description 5
- 230000000147 hypnotic effect Effects 0.000 title claims abstract description 5
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 38
- 150000003839 salts Chemical class 0.000 claims abstract description 73
- 229960004799 tryptophan Drugs 0.000 claims abstract description 50
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 claims abstract description 49
- 231100000252 nontoxic Toxicity 0.000 claims abstract description 46
- 230000003000 nontoxic effect Effects 0.000 claims abstract description 46
- 150000001875 compounds Chemical class 0.000 claims abstract description 45
- 230000000144 pharmacologic effect Effects 0.000 claims abstract description 5
- -1 1-(4-acetyl-amino-phenoxy)-3-isopropylamino-2-propanol Chemical compound 0.000 claims description 166
- 125000000217 alkyl group Chemical group 0.000 claims description 53
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 48
- 239000002253 acid Substances 0.000 claims description 36
- 125000003118 aryl group Chemical group 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- JZQKKSLKJUAGIC-UHFFFAOYSA-N pindolol Chemical compound CC(C)NCC(O)COC1=CC=CC2=C1C=CN2 JZQKKSLKJUAGIC-UHFFFAOYSA-N 0.000 claims description 10
- 229930195733 hydrocarbon Natural products 0.000 claims description 9
- 125000002950 monocyclic group Chemical group 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 239000004215 Carbon black (E152) Substances 0.000 claims description 7
- IUBSYMUCCVWXPE-UHFFFAOYSA-N metoprolol Chemical compound COCCC1=CC=C(OCC(O)CNC(C)C)C=C1 IUBSYMUCCVWXPE-UHFFFAOYSA-N 0.000 claims description 7
- 239000002775 capsule Substances 0.000 claims description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 6
- 125000003367 polycyclic group Chemical group 0.000 claims description 6
- DURULFYMVIFBIR-UHFFFAOYSA-N practolol Chemical compound CC(C)NCC(O)COC1=CC=C(NC(C)=O)C=C1 DURULFYMVIFBIR-UHFFFAOYSA-N 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 239000008298 dragée Substances 0.000 claims description 5
- AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- GZDBSFAQFPWZFV-UHFFFAOYSA-N 1-(2,3-dihydro-1h-inden-4-yloxy)-3-(propan-2-ylamino)propan-2-ol Chemical compound CC(C)NCC(O)COC1=CC=CC2=C1CCC2 GZDBSFAQFPWZFV-UHFFFAOYSA-N 0.000 claims description 3
- SAWHVYHGMYAXLH-UHFFFAOYSA-N 1-(3h-inden-4-yloxy)-3-(propan-2-ylamino)propan-2-ol Chemical compound CC(C)NCC(O)COC1=CC=CC2=C1CC=C2 SAWHVYHGMYAXLH-UHFFFAOYSA-N 0.000 claims description 3
- XVTVPGKWYHWYAD-UHFFFAOYSA-N 1-(propan-2-ylamino)-3-[2-(1-pyrrolyl)phenoxy]-2-propanol Chemical compound CC(C)NCC(O)COC1=CC=CC=C1N1C=CC=C1 XVTVPGKWYHWYAD-UHFFFAOYSA-N 0.000 claims description 3
- PAZJSJFMUHDSTF-UHFFFAOYSA-N alprenolol Chemical compound CC(C)NCC(O)COC1=CC=CC=C1CC=C PAZJSJFMUHDSTF-UHFFFAOYSA-N 0.000 claims description 3
- 125000002837 carbocyclic group Chemical group 0.000 claims description 3
- NXWGWUVGUSFQJC-UHFFFAOYSA-N mepindolol Chemical compound CC(C)NCC(O)COC1=CC=CC2=C1C=C(C)N2 NXWGWUVGUSFQJC-UHFFFAOYSA-N 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000003826 tablet Substances 0.000 claims description 2
- NXQMNKUGGYNLBY-UHFFFAOYSA-N toliprolol Chemical compound CC(C)NCC(O)COC1=CC=CC(C)=C1 NXQMNKUGGYNLBY-UHFFFAOYSA-N 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 13
- 150000003254 radicals Chemical class 0.000 description 30
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 20
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 16
- 230000007958 sleep Effects 0.000 description 16
- 125000001424 substituent group Chemical group 0.000 description 15
- 229920002472 Starch Polymers 0.000 description 14
- 125000003545 alkoxy group Chemical group 0.000 description 13
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 12
- 239000008107 starch Substances 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 235000019359 magnesium stearate Nutrition 0.000 description 10
- 229920002261 Corn starch Polymers 0.000 description 9
- 235000019759 Maize starch Nutrition 0.000 description 9
- 230000000875 corresponding effect Effects 0.000 description 9
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 9
- 125000003342 alkenyl group Chemical group 0.000 description 8
- 125000005115 alkyl carbamoyl group Chemical group 0.000 description 8
- 150000001721 carbon Chemical group 0.000 description 8
- 239000008119 colloidal silica Substances 0.000 description 8
- 239000000306 component Substances 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 8
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 8
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 229910052708 sodium Inorganic materials 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 125000004414 alkyl thio group Chemical group 0.000 description 7
- 125000005237 alkyleneamino group Chemical group 0.000 description 7
- 229940076279 serotonin Drugs 0.000 description 7
- 235000015424 sodium Nutrition 0.000 description 7
- 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 6
- 125000005037 alkyl phenyl group Chemical group 0.000 description 6
- 125000005281 alkyl ureido group Chemical group 0.000 description 6
- 125000003396 thiol group Chemical group [H]S* 0.000 description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- 125000003282 alkyl amino group Chemical group 0.000 description 5
- 125000001589 carboacyl group Chemical group 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 229920001223 polyethylene glycol Polymers 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- MYJOGYCKRILART-UHFFFAOYSA-N 1-[4-(2-methylsulfanylethoxy)phenoxy]-3-(propan-2-ylamino)propan-2-ol Chemical compound CSCCOC1=CC=C(OCC(O)CNC(C)C)C=C1 MYJOGYCKRILART-UHFFFAOYSA-N 0.000 description 4
- 241000282326 Felis catus Species 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 125000005236 alkanoylamino group Chemical group 0.000 description 4
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 description 4
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 125000001624 naphthyl group Chemical group 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 208000019116 sleep disease Diseases 0.000 description 4
- 235000019698 starch Nutrition 0.000 description 4
- 238000011282 treatment Methods 0.000 description 4
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 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 3
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 3
- 239000001828 Gelatine Substances 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 125000004442 acylamino group Chemical group 0.000 description 3
- 125000006193 alkinyl group Chemical group 0.000 description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 3
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 229920000159 gelatin Polymers 0.000 description 3
- 235000019322 gelatine Nutrition 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 230000000803 paradoxical effect Effects 0.000 description 3
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 3
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 3
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 230000036385 rapid eye movement (rem) sleep Effects 0.000 description 3
- 239000000600 sorbitol Substances 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- 235000012222 talc Nutrition 0.000 description 3
- 150000003626 triacylglycerols Chemical class 0.000 description 3
- BIHMFZKPHGYALQ-UHFFFAOYSA-N 1-(3-methylphenoxy)-1-(propan-2-ylamino)propan-2-ol Chemical compound CC(C)NC(C(C)O)OC1=CC=CC(C)=C1 BIHMFZKPHGYALQ-UHFFFAOYSA-N 0.000 description 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 2
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 2
- LDCYZAJDBXYCGN-VIFPVBQESA-N 5-hydroxy-L-tryptophan Chemical group C1=C(O)C=C2C(C[C@H](N)C(O)=O)=CNC2=C1 LDCYZAJDBXYCGN-VIFPVBQESA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-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
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 206010062519 Poor quality sleep Diseases 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 125000004423 acyloxy group Chemical group 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 125000003302 alkenyloxy group Chemical group 0.000 description 2
- 125000005108 alkenylthio group Chemical group 0.000 description 2
- 125000005036 alkoxyphenyl group Chemical group 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 210000004556 brain Anatomy 0.000 description 2
- 239000001506 calcium phosphate Substances 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000010685 fatty oil Substances 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 210000004051 gastric juice Anatomy 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 125000001041 indolyl group Chemical group 0.000 description 2
- 230000001939 inductive effect Effects 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 239000012188 paraffin wax Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 235000011007 phosphoric acid Nutrition 0.000 description 2
- 150000003016 phosphoric acids Chemical class 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- ZMRUPTIKESYGQW-UHFFFAOYSA-N propranolol hydrochloride Chemical compound [H+].[Cl-].C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 ZMRUPTIKESYGQW-UHFFFAOYSA-N 0.000 description 2
- 125000003373 pyrazinyl group Chemical group 0.000 description 2
- 125000005554 pyridyloxy group Chemical group 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 2
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- 239000002511 suppository base Substances 0.000 description 2
- 230000001629 suppression Effects 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical class [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 2
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- UWYVPFMHMJIBHE-OWOJBTEDSA-N (e)-2-hydroxybut-2-enedioic acid Chemical compound OC(=O)\C=C(\O)C(O)=O UWYVPFMHMJIBHE-OWOJBTEDSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- 125000004518 1,2,5-thiadiazol-3-yl group Chemical group S1N=C(C=N1)* 0.000 description 1
- HIOSGQZZOJVIJJ-UHFFFAOYSA-N 1-(2-methylphenyl)sulfanyl-3-(propan-2-ylamino)propan-2-ol Chemical compound CC(C)NCC(O)CSC1=CC=CC=C1C HIOSGQZZOJVIJJ-UHFFFAOYSA-N 0.000 description 1
- OMTHEGLYCMFVCT-UHFFFAOYSA-N 1-(9h-fluoren-4-yloxy)-3-(propan-2-ylamino)propan-2-ol Chemical compound C1C2=CC=CC=C2C2=C1C=CC=C2OCC(O)CNC(C)C OMTHEGLYCMFVCT-UHFFFAOYSA-N 0.000 description 1
- FYOGTFROMBUNKU-UHFFFAOYSA-N 1-(propan-2-ylamino)-3-(2-prop-2-ynoxyphenoxy)propan-2-ol Chemical compound CC(C)NCC(O)COC1=CC=CC=C1OCC#C FYOGTFROMBUNKU-UHFFFAOYSA-N 0.000 description 1
- JYYSFYYPIFXZEP-UHFFFAOYSA-N 1-[(4-morpholin-4-yl-1,2,5-thiadiazol-3-yl)oxy]-3-(propan-2-ylamino)propan-2-ol Chemical compound CC(C)NCC(O)COC1=NSN=C1N1CCOCC1 JYYSFYYPIFXZEP-UHFFFAOYSA-N 0.000 description 1
- WGJVNJGGPWONPI-UHFFFAOYSA-N 1-[2-(hydroxymethyl)phenoxy]-3-(propan-2-ylamino)propan-2-ol Chemical compound CC(C)NCC(O)COC1=CC=CC=C1CO WGJVNJGGPWONPI-UHFFFAOYSA-N 0.000 description 1
- MEKGXKWXYHQTJA-UHFFFAOYSA-N 1-[2-(methoxymethyl)phenoxy]-3-(propan-2-ylamino)propan-2-ol Chemical compound COCC1=CC=CC=C1OCC(O)CNC(C)C MEKGXKWXYHQTJA-UHFFFAOYSA-N 0.000 description 1
- YTRGXYPNJSCHJX-UHFFFAOYSA-N 1-[4-(2-methoxyethyl)phenoxy]-1-(propan-2-ylamino)propan-2-ol Chemical compound COCCC1=CC=C(OC(NC(C)C)C(C)O)C=C1 YTRGXYPNJSCHJX-UHFFFAOYSA-N 0.000 description 1
- UGMARLGXBJNQQA-UHFFFAOYSA-N 1-amino-1-(2-cyclopropylphenoxy)-4-methylpentan-2-ol Chemical compound C1(CC1)C1=C(OC(C(CC(C)C)O)N)C=CC=C1 UGMARLGXBJNQQA-UHFFFAOYSA-N 0.000 description 1
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 1
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- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229940100486 rice starch Drugs 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 230000037322 slow-wave sleep Effects 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 239000012439 solid excipient Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 229940078499 tricalcium phosphate Drugs 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- 229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229940100445 wheat starch Drugs 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
- A61K31/405—Indole-alkanecarboxylic acids; Derivatives thereof, e.g. tryptophan, indomethacin
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Indole Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH7275 | 1975-01-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1063026A true CA1063026A (en) | 1979-09-25 |
Family
ID=4178653
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA242,911A Expired CA1063026A (en) | 1975-01-06 | 1976-01-02 | Pharmaceutical preparation for hypnotics |
Country Status (13)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4433004A (en) * | 1979-07-11 | 1984-02-21 | Tokyo Shibaura Denki Kabushiki Kaisha | Semiconductor device and a method for manufacturing the same |
-
1975
- 1975-12-22 NZ NZ179621A patent/NZ179621A/xx unknown
-
1976
- 1976-01-02 DE DE19762600070 patent/DE2600070A1/de not_active Withdrawn
- 1976-01-02 CA CA242,911A patent/CA1063026A/en not_active Expired
- 1976-01-02 FR FR7600015A patent/FR2296414A1/fr active Granted
- 1976-01-05 IE IE12/76A patent/IE42230B1/en unknown
- 1976-01-05 GB GB144/76A patent/GB1531091A/en not_active Expired
- 1976-01-05 BE BE163297A patent/BE837295A/xx unknown
- 1976-01-05 AU AU10003/76A patent/AU500434B2/en not_active Expired
- 1976-01-05 ES ES444083A patent/ES444083A1/es not_active Expired
- 1976-01-05 ZA ZA00760027A patent/ZA7627B/xx unknown
- 1976-01-05 NL NL7600044A patent/NL7600044A/xx not_active Application Discontinuation
- 1976-01-05 IL IL48786A patent/IL48786A/xx unknown
- 1976-01-06 JP JP51000125A patent/JPS5191336A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| BE837295A (fr) | 1976-07-05 |
| IE42230L (en) | 1976-07-06 |
| JPS5191336A (enrdf_load_stackoverflow) | 1976-08-10 |
| DE2600070A1 (de) | 1976-07-15 |
| IL48786A (en) | 1978-12-17 |
| IL48786A0 (en) | 1976-03-31 |
| AU500434B2 (en) | 1979-05-24 |
| GB1531091A (en) | 1978-11-01 |
| NL7600044A (nl) | 1976-07-08 |
| ES444083A1 (es) | 1977-05-01 |
| IE42230B1 (en) | 1980-07-02 |
| AU1000376A (en) | 1977-07-14 |
| FR2296414B1 (enrdf_load_stackoverflow) | 1981-12-31 |
| FR2296414A1 (fr) | 1976-07-30 |
| NZ179621A (en) | 1978-04-28 |
| ZA7627B (en) | 1976-12-29 |
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