FI73671C - Foerfarande foer framstaellning av farmakologiskt vaerdefullt tetratzolderivat. - Google Patents
Foerfarande foer framstaellning av farmakologiskt vaerdefullt tetratzolderivat. Download PDFInfo
- Publication number
- FI73671C FI73671C FI810394A FI810394A FI73671C FI 73671 C FI73671 C FI 73671C FI 810394 A FI810394 A FI 810394A FI 810394 A FI810394 A FI 810394A FI 73671 C FI73671 C FI 73671C
- Authority
- FI
- Finland
- Prior art keywords
- alkyl
- tetrazol
- methyl
- phenyl
- ethyl
- Prior art date
Links
- -1 amino, nitro, aminosulfonyl Chemical group 0.000 claims description 77
- 239000000203 mixture Substances 0.000 claims description 64
- 238000000034 method Methods 0.000 claims description 35
- 229910052757 nitrogen Inorganic materials 0.000 claims description 29
- 150000001412 amines Chemical class 0.000 claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 150000003536 tetrazoles Chemical class 0.000 claims description 5
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- VSEAAEQOQBMPQF-UHFFFAOYSA-N morpholin-3-one Chemical compound O=C1COCCN1 VSEAAEQOQBMPQF-UHFFFAOYSA-N 0.000 claims description 3
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- 125000000034 thioazolyl group Chemical group 0.000 claims description 3
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 2
- 239000002594 sorbent Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 5
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 2
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000002993 cycloalkylene group Chemical group 0.000 claims 1
- 150000002780 morpholines Chemical class 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical compound O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 claims 1
- 239000007788 liquid Substances 0.000 description 103
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 90
- 150000001875 compounds Chemical class 0.000 description 55
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 48
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 43
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 42
- 239000000243 solution Substances 0.000 description 40
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 34
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 32
- 238000003756 stirring Methods 0.000 description 29
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 25
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 25
- 238000001816 cooling Methods 0.000 description 25
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 24
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 23
- 239000002904 solvent Substances 0.000 description 23
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 22
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- 229920006395 saturated elastomer Polymers 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 238000000921 elemental analysis Methods 0.000 description 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 13
- 239000011780 sodium chloride Substances 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 11
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 11
- 235000017557 sodium bicarbonate Nutrition 0.000 description 11
- 239000013078 crystal Substances 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 10
- 239000010410 layer Substances 0.000 description 10
- 239000000843 powder Substances 0.000 description 10
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 238000004440 column chromatography Methods 0.000 description 8
- 229950001902 dimevamide Drugs 0.000 description 8
- AGVKXDPPPSLISR-UHFFFAOYSA-N n-ethylcyclohexanamine Chemical compound CCNC1CCCCC1 AGVKXDPPPSLISR-UHFFFAOYSA-N 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 7
- 150000008065 acid anhydrides Chemical class 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- IPWFJLQDVFKJDU-UHFFFAOYSA-N pentanamide Chemical compound CCCCC(N)=O IPWFJLQDVFKJDU-UHFFFAOYSA-N 0.000 description 7
- FWKWZHMTRDZWSN-UHFFFAOYSA-N 4-(1-methyltetrazol-5-yl)butanethioic s-acid Chemical compound CN1N=NN=C1CCCC(S)=O FWKWZHMTRDZWSN-UHFFFAOYSA-N 0.000 description 6
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 229920002472 Starch Polymers 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 150000007514 bases Chemical class 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- 235000019698 starch Nutrition 0.000 description 6
- 239000003826 tablet Substances 0.000 description 6
- 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 5
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 235000011121 sodium hydroxide Nutrition 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 4
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 108010010803 Gelatin Proteins 0.000 description 4
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 4
- WPLXTOVHRYJKSG-UHFFFAOYSA-N butanethioamide Chemical compound CCCC(N)=S WPLXTOVHRYJKSG-UHFFFAOYSA-N 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 238000003818 flash chromatography Methods 0.000 description 4
- 230000002496 gastric effect Effects 0.000 description 4
- 239000008273 gelatin Substances 0.000 description 4
- 229920000159 gelatin Polymers 0.000 description 4
- 235000019322 gelatine Nutrition 0.000 description 4
- 235000011852 gelatine desserts Nutrition 0.000 description 4
- 239000008103 glucose Substances 0.000 description 4
- 230000002140 halogenating effect Effects 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 239000008101 lactose Substances 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 235000011181 potassium carbonates Nutrition 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 3
- 239000005995 Aluminium silicate Substances 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 235000012211 aluminium silicate Nutrition 0.000 description 3
- ASGJEMPQQVNTGO-UHFFFAOYSA-N benzene chloroform Chemical compound C(Cl)(Cl)Cl.C1=CC=CC=C1.C1=CC=CC=C1 ASGJEMPQQVNTGO-UHFFFAOYSA-N 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 238000006664 bond formation reaction Methods 0.000 description 3
- DGAODIKUWGRDBO-UHFFFAOYSA-N butanethioic s-acid Chemical compound CCCC(O)=S DGAODIKUWGRDBO-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 150000008282 halocarbons Chemical class 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 3
- IZQBIHAPLPPWQA-UHFFFAOYSA-N n-(furan-2-ylmethyl)-4-(1-methyltetrazol-5-yl)sulfanylbutanamide Chemical compound CN1N=NN=C1SCCCC(=O)NCC1=CC=CO1 IZQBIHAPLPPWQA-UHFFFAOYSA-N 0.000 description 3
- RWGGSNKUNTZVTC-UHFFFAOYSA-N n-cyclohexyl-n-ethyl-4-(1-methyltetrazol-5-yl)sulfanylbutanamide Chemical compound N=1N=NN(C)C=1SCCCC(=O)N(CC)C1CCCCC1 RWGGSNKUNTZVTC-UHFFFAOYSA-N 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000000546 pharmaceutical excipient Substances 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 239000006187 pill Substances 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 229960003975 potassium Drugs 0.000 description 3
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 235000017550 sodium carbonate Nutrition 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- OMAFFHIGWTVZOH-UHFFFAOYSA-N 1-methyltetrazole Chemical compound CN1C=NN=N1 OMAFFHIGWTVZOH-UHFFFAOYSA-N 0.000 description 2
- HOZLOOPIXHWKCI-UHFFFAOYSA-N 2-chloro-n-methylacetamide Chemical compound CNC(=O)CCl HOZLOOPIXHWKCI-UHFFFAOYSA-N 0.000 description 2
- NPCLRBQYESMUPD-UHFFFAOYSA-N 2-methylpropanethioamide Chemical compound CC(C)C(N)=S NPCLRBQYESMUPD-UHFFFAOYSA-N 0.000 description 2
- ANOUKFYBOAKOIR-UHFFFAOYSA-N 3,4-dimethoxyphenylethylamine Chemical compound COC1=CC=C(CCN)C=C1OC ANOUKFYBOAKOIR-UHFFFAOYSA-N 0.000 description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 2
- NNRKYKZDMXGELT-UHFFFAOYSA-N 4-(1-methyltetrazol-5-yl)sulfanyl-1-morpholin-4-ylbutan-1-one Chemical compound CN1N=NN=C1SCCCC(=O)N1CCOCC1 NNRKYKZDMXGELT-UHFFFAOYSA-N 0.000 description 2
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 2
- XTUVJUMINZSXGF-UHFFFAOYSA-N N-methylcyclohexylamine Chemical compound CNC1CCCCC1 XTUVJUMINZSXGF-UHFFFAOYSA-N 0.000 description 2
- PAMIQIKDUOTOBW-UHFFFAOYSA-N N-methylcyclohexylamine Natural products CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
- 102000057297 Pepsin A Human genes 0.000 description 2
- 108090000284 Pepsin A Proteins 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 238000003436 Schotten-Baumann reaction Methods 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- 230000000767 anti-ulcer Effects 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 229940110456 cocoa butter Drugs 0.000 description 2
- 235000019868 cocoa butter Nutrition 0.000 description 2
- 239000012050 conventional carrier Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000012024 dehydrating agents Substances 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 239000007884 disintegrant Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 2
- 229960003750 ethyl chloride Drugs 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 231100000636 lethal dose Toxicity 0.000 description 2
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- LSJDHXCCSZHRTR-UHFFFAOYSA-N n-[2-(3,4-dimethoxyphenyl)ethyl]-4-(1-methyltetrazol-5-yl)butanethioamide Chemical compound C1=C(OC)C(OC)=CC=C1CCNC(=S)CCCC1=NN=NN1C LSJDHXCCSZHRTR-UHFFFAOYSA-N 0.000 description 2
- HXLXXGMLDGGHSQ-UHFFFAOYSA-N n-cyclohexyl-5-(1-cyclohexyltetrazol-5-yl)-n-ethylpentanamide Chemical compound N=1N=NN(C2CCCCC2)C=1CCCCC(=O)N(CC)C1CCCCC1 HXLXXGMLDGGHSQ-UHFFFAOYSA-N 0.000 description 2
- VDZAMAJQDOCZHP-UHFFFAOYSA-N n-ethyl-5-[1-(3-ethylcyclohexyl)tetrazol-5-yl]pentanamide Chemical compound CCNC(=O)CCCCC1=NN=NN1C1CC(CC)CCC1 VDZAMAJQDOCZHP-UHFFFAOYSA-N 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 229940111202 pepsin Drugs 0.000 description 2
- 230000001175 peptic effect Effects 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 235000011118 potassium hydroxide Nutrition 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- LZFBOQOMPIKJBI-ISVAXAHUSA-N (2r,3r)-3-(2,4-difluorophenyl)-3-hydroxy-2-methyl-4-(1,2,4-triazol-1-yl)butanethioamide Chemical compound C([C@@](O)([C@H](C(N)=S)C)C=1C(=CC(F)=CC=1)F)N1C=NC=N1 LZFBOQOMPIKJBI-ISVAXAHUSA-N 0.000 description 1
- OGFAWKRXZLGJSK-UHFFFAOYSA-N 1-(2,4-dihydroxyphenyl)-2-(4-nitrophenyl)ethanone Chemical compound OC1=CC(O)=CC=C1C(=O)CC1=CC=C([N+]([O-])=O)C=C1 OGFAWKRXZLGJSK-UHFFFAOYSA-N 0.000 description 1
- WNIHCHNLVZBXRY-UHFFFAOYSA-N 1-(4-acetylpiperazin-1-yl)-4-(1-methyltetrazol-5-yl)sulfanylbutan-1-one Chemical compound C1CN(C(=O)C)CCN1C(=O)CCCSC1=NN=NN1C WNIHCHNLVZBXRY-UHFFFAOYSA-N 0.000 description 1
- IYYJBAVEZPDVBH-UHFFFAOYSA-N 1-(4-methylpiperazin-1-yl)-4-(1-phenyltetrazol-5-yl)butan-1-one Chemical compound C1CN(C)CCN1C(=O)CCCC1=NN=NN1C1=CC=CC=C1 IYYJBAVEZPDVBH-UHFFFAOYSA-N 0.000 description 1
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 1
- WNWHHMBRJJOGFJ-UHFFFAOYSA-N 16-methylheptadecan-1-ol Chemical class CC(C)CCCCCCCCCCCCCCCO WNWHHMBRJJOGFJ-UHFFFAOYSA-N 0.000 description 1
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Chemical compound C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 description 1
- PZJFUNZDCRKXPZ-UHFFFAOYSA-N 2,5-dihydro-1h-tetrazole Chemical compound C1NNN=N1 PZJFUNZDCRKXPZ-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- CUTKXXKVSDIVMV-UHFFFAOYSA-N 2-chloro-n-cyclohexyl-n-ethylacetamide Chemical compound ClCC(=O)N(CC)C1CCCCC1 CUTKXXKVSDIVMV-UHFFFAOYSA-N 0.000 description 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
- XZMQDDPUEIBDBQ-UHFFFAOYSA-N 3-(1-ethyltetrazol-5-yl)-n,2-dimethylpropanethioamide Chemical compound CCN1N=NN=C1CC(C)C(=S)NC XZMQDDPUEIBDBQ-UHFFFAOYSA-N 0.000 description 1
- DLILMAIALIVQNX-UHFFFAOYSA-N 3-[(1-ethyltetrazol-5-yl)methylsulfanyl]propanamide Chemical compound CCN1N=NN=C1CSCCC(N)=O DLILMAIALIVQNX-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 1
- IHLAIUNRFJCFGO-UHFFFAOYSA-N 3-chloro-n-cyclohexyl-n-ethylpropanamide Chemical compound ClCCC(=O)N(CC)C1CCCCC1 IHLAIUNRFJCFGO-UHFFFAOYSA-N 0.000 description 1
- DDAZLSBAGZRSPG-UHFFFAOYSA-N 4-(1-cyclohexyltetrazol-5-yl)butanethioic s-acid Chemical compound SC(=O)CCCC1=NN=NN1C1CCCCC1 DDAZLSBAGZRSPG-UHFFFAOYSA-N 0.000 description 1
- CPTWNLXGJFEPKI-UHFFFAOYSA-N 4-(1-methyltetrazol-5-yl)-n-pentylbutanethioamide Chemical compound CCCCCNC(=S)CCCC1=NN=NN1C CPTWNLXGJFEPKI-UHFFFAOYSA-N 0.000 description 1
- VMGGCVCRZZACFG-UHFFFAOYSA-N 4-(1-methyltetrazol-5-yl)sulfanyl-1-piperidin-1-ylbutan-1-one Chemical compound CN1N=NN=C1SCCCC(=O)N1CCCCC1 VMGGCVCRZZACFG-UHFFFAOYSA-N 0.000 description 1
- NKTAHXSUKZVZEF-UHFFFAOYSA-N 4-[1-(2-methoxycyclohexyl)tetrazol-5-yl]butanethioic s-acid Chemical compound COC1CCCCC1N1C(CCCC(S)=O)=NN=N1 NKTAHXSUKZVZEF-UHFFFAOYSA-N 0.000 description 1
- KVCQTKNUUQOELD-UHFFFAOYSA-N 4-amino-n-[1-(3-chloro-2-fluoroanilino)-6-methylisoquinolin-5-yl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N=1C=CC2=C(NC(=O)C=3C4=NC=NC(N)=C4SC=3)C(C)=CC=C2C=1NC1=CC=CC(Cl)=C1F KVCQTKNUUQOELD-UHFFFAOYSA-N 0.000 description 1
- VKCLBNXEILMXBP-UHFFFAOYSA-N 4-chloro-n-cyclohexyl-n-ethylbutanamide Chemical compound ClCCCC(=O)N(CC)C1CCCCC1 VKCLBNXEILMXBP-UHFFFAOYSA-N 0.000 description 1
- HQWFWBNJUPPCDU-UHFFFAOYSA-N 4-chloro-n-cyclohexyl-n-methylbutanamide Chemical compound ClCCCC(=O)N(C)C1CCCCC1 HQWFWBNJUPPCDU-UHFFFAOYSA-N 0.000 description 1
- CDIIZULDSLKBKV-UHFFFAOYSA-N 4-chlorobutanoyl chloride Chemical compound ClCCCC(Cl)=O CDIIZULDSLKBKV-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- GNGZZWTXFNFCMU-UHFFFAOYSA-N 4-n,4-n-dimethylcyclohexane-1,4-diamine Chemical compound CN(C)C1CCC(N)CC1 GNGZZWTXFNFCMU-UHFFFAOYSA-N 0.000 description 1
- GQZMQJIWKPETKN-UHFFFAOYSA-N 5-(1-cyclohexyltetrazol-5-yl)pentanoic acid Chemical compound OC(=O)CCCCC1=NN=NN1C1CCCCC1 GQZMQJIWKPETKN-UHFFFAOYSA-N 0.000 description 1
- XNGQVRGOTHGYJR-UHFFFAOYSA-N 5-(1-methyltetrazol-5-yl)pentanoic acid Chemical compound CN1N=NN=C1CCCCC(O)=O XNGQVRGOTHGYJR-UHFFFAOYSA-N 0.000 description 1
- MTIITSWTSGKZAE-UHFFFAOYSA-N 5-(1-phenyltetrazol-5-yl)-n-(1,3-thiazol-2-yl)pentanamide Chemical compound N=1C=CSC=1NC(=O)CCCCC1=NN=NN1C1=CC=CC=C1 MTIITSWTSGKZAE-UHFFFAOYSA-N 0.000 description 1
- QZGWXTQDPDFMFF-UHFFFAOYSA-N 5-(1-phenyltetrazol-5-yl)pentanoic acid Chemical compound OC(=O)CCCCC1=NN=NN1C1=CC=CC=C1 QZGWXTQDPDFMFF-UHFFFAOYSA-N 0.000 description 1
- QVMQSOGTBSMUQG-UHFFFAOYSA-N 5-(chloromethyl)-1-methyltetrazole Chemical compound CN1N=NN=C1CCl QVMQSOGTBSMUQG-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- MESUBWNVBPVJHY-UHFFFAOYSA-N C(=O)O.Br(=O)(=O)OC Chemical compound C(=O)O.Br(=O)(=O)OC MESUBWNVBPVJHY-UHFFFAOYSA-N 0.000 description 1
- MUUDAPQSDIXSKC-UHFFFAOYSA-N C(C)N(C(C(CC1=NN=NN1C1=CC=CC=C1)C)=S)CC Chemical compound C(C)N(C(C(CC1=NN=NN1C1=CC=CC=C1)C)=S)CC MUUDAPQSDIXSKC-UHFFFAOYSA-N 0.000 description 1
- XBDKBYUUZYEKTP-UHFFFAOYSA-N C(CC)N(C(CCC(C)C1=NN=NN1C1=CC=CC=C1)=O)CCC Chemical compound C(CC)N(C(CCC(C)C1=NN=NN1C1=CC=CC=C1)=O)CCC XBDKBYUUZYEKTP-UHFFFAOYSA-N 0.000 description 1
- BYXCRLYOTXDNAB-UHFFFAOYSA-N C1(=CC=CC=C1)CCNC(CCCC1=NN=NN1C)=S Chemical compound C1(=CC=CC=C1)CCNC(CCCC1=NN=NN1C)=S BYXCRLYOTXDNAB-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- BVLJOTCQAZXCQI-UHFFFAOYSA-N N-cyclohexyl-N-ethyl-5-[1-(4-methoxyphenyl)tetrazol-5-yl]pentanamide Chemical compound N=1N=NN(C=2C=CC(OC)=CC=2)C=1CCCCC(=O)N(CC)C1CCCCC1 BVLJOTCQAZXCQI-UHFFFAOYSA-N 0.000 description 1
- 208000008469 Peptic Ulcer Diseases 0.000 description 1
- 201000005702 Pertussis Diseases 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 241000700157 Rattus norvegicus Species 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 244000297179 Syringa vulgaris Species 0.000 description 1
- 235000004338 Syringa vulgaris Nutrition 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- LXRZVMYMQHNYJB-UNXOBOICSA-N [(1R,2S,4R)-4-[[5-[4-[(1R)-7-chloro-1,2,3,4-tetrahydroisoquinolin-1-yl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound CC1=C(C=C(S1)C(=O)C1=C(N[C@H]2C[C@H](O)[C@@H](COS(N)(=O)=O)C2)N=CN=C1)[C@@H]1NCCC2=C1C=C(Cl)C=C2 LXRZVMYMQHNYJB-UNXOBOICSA-N 0.000 description 1
- GHVZOJONCUEWAV-UHFFFAOYSA-N [K].CCO Chemical compound [K].CCO GHVZOJONCUEWAV-UHFFFAOYSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 230000003266 anti-allergic effect Effects 0.000 description 1
- 230000001078 anti-cholinergic effect Effects 0.000 description 1
- 230000003373 anti-fouling effect Effects 0.000 description 1
- 229940124599 anti-inflammatory drug Drugs 0.000 description 1
- 230000001166 anti-perspirative effect Effects 0.000 description 1
- 239000003213 antiperspirant Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000004067 bulking agent Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- OQNGCCWBHLEQFN-UHFFFAOYSA-N chloroform;hexane Chemical compound ClC(Cl)Cl.CCCCCC OQNGCCWBHLEQFN-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000008119 colloidal silica Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- DMSZORWOGDLWGN-UHFFFAOYSA-N ctk1a3526 Chemical compound NP(N)(N)=O DMSZORWOGDLWGN-UHFFFAOYSA-N 0.000 description 1
- 239000012973 diazabicyclooctane Substances 0.000 description 1
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 230000002183 duodenal effect Effects 0.000 description 1
- 208000000718 duodenal ulcer Diseases 0.000 description 1
- 239000002662 enteric coated tablet Substances 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- XCPXPFNKTCFWTA-UHFFFAOYSA-N ethyl carbonobromidate Chemical compound CCOC(Br)=O XCPXPFNKTCFWTA-UHFFFAOYSA-N 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000007941 film coated tablet Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 230000030136 gastric emptying Effects 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 229960000905 indomethacin Drugs 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000000314 lubricant Substances 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
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- UOBSVARXACCLLH-UHFFFAOYSA-N monomethyl adipate Chemical compound COC(=O)CCCCC(O)=O UOBSVARXACCLLH-UHFFFAOYSA-N 0.000 description 1
- RHVUNERAOPZZOB-UHFFFAOYSA-N n,n-diethyl-4-(1-phenyltetrazol-5-yl)butanethioamide Chemical compound CCN(CC)C(=S)CCCC1=NN=NN1C1=CC=CC=C1 RHVUNERAOPZZOB-UHFFFAOYSA-N 0.000 description 1
- HJMYLFFPKTVTLN-UHFFFAOYSA-N n,n-diethyl-5-(1-phenyltetrazol-5-yl)pentanamide Chemical compound CCN(CC)C(=O)CCCCC1=NN=NN1C1=CC=CC=C1 HJMYLFFPKTVTLN-UHFFFAOYSA-N 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- HIOLQWKFQOZUKR-UHFFFAOYSA-N n-(4-methylcyclohexyl)-4-(1-methyltetrazol-5-yl)butanethioamide Chemical compound C1CC(C)CCC1NC(=S)CCCC1=NN=NN1C HIOLQWKFQOZUKR-UHFFFAOYSA-N 0.000 description 1
- NSGZWAOTMQTMQV-UHFFFAOYSA-N n-butyl-3-(1-methyltetrazol-5-yl)propanethioamide Chemical compound CCCCNC(=S)CCC1=NN=NN1C NSGZWAOTMQTMQV-UHFFFAOYSA-N 0.000 description 1
- INRRJRMLZVMYOI-UHFFFAOYSA-N n-butyl-5-(1-methyltetrazol-5-yl)pentanethioamide Chemical compound CCCCNC(=S)CCCCC1=NN=NN1C INRRJRMLZVMYOI-UHFFFAOYSA-N 0.000 description 1
- CXXKGMZGCUZFAV-UHFFFAOYSA-N n-butyl-5-(1-phenyltetrazol-5-yl)pentanamide Chemical compound CCCCNC(=O)CCCCC1=NN=NN1C1=CC=CC=C1 CXXKGMZGCUZFAV-UHFFFAOYSA-N 0.000 description 1
- BSQYHCRAVZTITA-UHFFFAOYSA-N n-cyclohexyl-4-(1-methyltetrazol-5-yl)sulfanylbutanamide Chemical compound CN1N=NN=C1SCCCC(=O)NC1CCCCC1 BSQYHCRAVZTITA-UHFFFAOYSA-N 0.000 description 1
- ZTWBFLALLWDVQG-UHFFFAOYSA-N n-cyclohexyl-n-[2-(3,4-dimethoxyphenyl)ethyl]-4-(1-methyltetrazol-5-yl)sulfanylbutanamide Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C(=O)CCCSC=1N(N=NN=1)C)C1CCCCC1 ZTWBFLALLWDVQG-UHFFFAOYSA-N 0.000 description 1
- RDAFXSPQODNGDE-UHFFFAOYSA-N n-cyclohexyl-n-ethyl-5-(1-methyltetrazol-5-yl)sulfanylpentanamide Chemical compound N=1N=NN(C)C=1SCCCCC(=O)N(CC)C1CCCCC1 RDAFXSPQODNGDE-UHFFFAOYSA-N 0.000 description 1
- KEJRVBBZOIUEDA-UHFFFAOYSA-N n-cyclohexyl-n-ethyl-5-(1-phenyltetrazol-5-yl)pentanamide Chemical compound N=1N=NN(C=2C=CC=CC=2)C=1CCCCC(=O)N(CC)C1CCCCC1 KEJRVBBZOIUEDA-UHFFFAOYSA-N 0.000 description 1
- SOEVUSLNCDIHMM-UHFFFAOYSA-N n-ethyl-2-(1-ethyltetrazol-5-yl)propanethioamide Chemical compound CCNC(=S)C(C)C1=NN=NN1CC SOEVUSLNCDIHMM-UHFFFAOYSA-N 0.000 description 1
- GUSUZHBGFHVORB-UHFFFAOYSA-N n-ethyl-2-methyl-3-(1-methyltetrazol-5-yl)propanethioamide Chemical compound CCNC(=S)C(C)CC1=NN=NN1C GUSUZHBGFHVORB-UHFFFAOYSA-N 0.000 description 1
- DKGNJSFIVVAFFU-UHFFFAOYSA-N n-ethyl-3-(1-ethyltetrazol-5-yl)-2-methylpropanethioamide Chemical compound CCNC(=S)C(C)CC1=NN=NN1CC DKGNJSFIVVAFFU-UHFFFAOYSA-N 0.000 description 1
- LEXWXZWWPZXJJK-UHFFFAOYSA-N n-ethyl-4-(1-ethyltetrazol-5-yl)butanethioamide Chemical compound CCNC(=S)CCCC1=NN=NN1CC LEXWXZWWPZXJJK-UHFFFAOYSA-N 0.000 description 1
- DECCIDWRTKSIGZ-UHFFFAOYSA-N n-ethyl-4-(1-ethyltetrazol-5-yl)pentanethioamide Chemical compound CCNC(=S)CCC(C)C1=NN=NN1CC DECCIDWRTKSIGZ-UHFFFAOYSA-N 0.000 description 1
- WWUFYMKTLBBINN-UHFFFAOYSA-N n-ethyl-4-[(1-ethyltetrazol-5-yl)methylsulfanyl]butanamide Chemical compound CCNC(=O)CCCSCC1=NN=NN1CC WWUFYMKTLBBINN-UHFFFAOYSA-N 0.000 description 1
- FVNPXTVIUXTERA-UHFFFAOYSA-N n-ethyl-n-phenyl-5-(1-phenyltetrazol-5-yl)pentanamide Chemical compound C=1C=CC=CC=1N(CC)C(=O)CCCCC1=NN=NN1C1=CC=CC=C1 FVNPXTVIUXTERA-UHFFFAOYSA-N 0.000 description 1
- HEKDAOHEFWZAGA-UHFFFAOYSA-N n-hexyl-5-(1-phenyltetrazol-5-yl)pentanamide Chemical compound CCCCCCNC(=O)CCCCC1=NN=NN1C1=CC=CC=C1 HEKDAOHEFWZAGA-UHFFFAOYSA-N 0.000 description 1
- ZWULECGKJHSRJS-UHFFFAOYSA-N o-methyl 4-(1-methyltetrazol-5-yl)butanethioate Chemical compound COC(=S)CCCC1=NN=NN1C ZWULECGKJHSRJS-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical compound OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 description 1
- UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- 229940080818 propionamide Drugs 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 239000007940 sugar coated tablet Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000032258 transport Effects 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 210000001215 vagina Anatomy 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12471080A | 1980-02-26 | 1980-02-26 | |
| US12471080 | 1980-02-26 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI810394L FI810394L (fi) | 1981-08-27 |
| FI73671B FI73671B (fi) | 1987-07-31 |
| FI73671C true FI73671C (fi) | 1987-11-09 |
Family
ID=22416399
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI810394A FI73671C (fi) | 1980-02-26 | 1981-02-11 | Foerfarande foer framstaellning av farmakologiskt vaerdefullt tetratzolderivat. |
Country Status (9)
| Country | Link |
|---|---|
| AT (1) | AT375352B (de) |
| DK (1) | DK162047C (de) |
| FI (1) | FI73671C (de) |
| MX (1) | MX6776E (de) |
| NO (1) | NO157502C (de) |
| PH (1) | PH17505A (de) |
| PT (1) | PT72568B (de) |
| SU (1) | SU1400507A3 (de) |
| ZA (1) | ZA81961B (de) |
-
1981
- 1981-02-11 FI FI810394A patent/FI73671C/fi not_active IP Right Cessation
- 1981-02-13 ZA ZA00810961A patent/ZA81961B/xx unknown
- 1981-02-24 DK DK83381A patent/DK162047C/da not_active IP Right Cessation
- 1981-02-25 PT PT7256881A patent/PT72568B/pt unknown
- 1981-02-25 NO NO810637A patent/NO157502C/no unknown
- 1981-02-25 PH PH25265A patent/PH17505A/en unknown
- 1981-02-26 MX MX932281U patent/MX6776E/es unknown
- 1981-02-26 AT AT89381A patent/AT375352B/de not_active IP Right Cessation
-
1982
- 1982-05-04 SU SU823430794A patent/SU1400507A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| NO157502B (no) | 1987-12-21 |
| PH17505A (en) | 1984-09-07 |
| DK83381A (da) | 1981-08-27 |
| DK162047B (da) | 1991-09-09 |
| FI73671B (fi) | 1987-07-31 |
| PT72568B (pt) | 1982-02-17 |
| ZA81961B (en) | 1982-03-31 |
| NO157502C (no) | 1988-03-30 |
| AT375352B (de) | 1984-07-25 |
| MX6776E (es) | 1986-07-10 |
| NO810637L (no) | 1981-08-27 |
| SU1400507A3 (ru) | 1988-05-30 |
| ATA89381A (de) | 1983-12-15 |
| PT72568A (pt) | 1981-03-01 |
| DK162047C (da) | 1992-02-10 |
| FI810394L (fi) | 1981-08-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| TW210998B (de) | ||
| US9421196B2 (en) | Amides as modulators of sodium channels | |
| AU644054B2 (en) | Benzoisothiazole and benzoisoxazole-3-carboxamides | |
| JP6425724B2 (ja) | Ｃｆｔｒモジュレーターとしてのチエノ［２，３−ｃ］ピラン | |
| US20160009743A1 (en) | Prodrugs of pyridone amides useful as modulators of sodium channels | |
| NO180540B1 (no) | Analogifremgangsmate for fremstilling av terapeutisk aktiv cyklisk amidderivat | |
| PL177031B1 (pl) | Nowe sulfonyloaminopirymidyny, sposób ich wytwarzania oraz zawierające je preparaty farmaceutyczne | |
| EA018988B1 (ru) | Активаторы глюкокиназы | |
| EP3126360A1 (de) | Sulfonamidverbindungen als spannungsabhängige natriumkanalmodulatoren | |
| EP0748317A1 (de) | Thiazolidin-4-on-derivate | |
| CA2053527C (en) | Pyridine derivatives, their production and use | |
| JP2024028642A (ja) | カンナビノイド受容体部分アゴニストとしてのインダゾール誘導体 | |
| NO146571B (no) | Analogifremgangsmaate ved fremstilling av anti-inflammatorisk aktive imidazoler | |
| FI73671C (fi) | Foerfarande foer framstaellning av farmakologiskt vaerdefullt tetratzolderivat. | |
| WO1988003136A1 (fr) | Composes de piperazine et leur utilisation medicinale | |
| NO844120L (no) | Tiazolinderivater og fremgangsmaate for dets fremstilling | |
| NO322109B1 (no) | Vitronektinreseporantagonister | |
| US5714501A (en) | Piperidine derivatives | |
| AU2006305769B2 (en) | Salts of modulators of PPAR and methods of treating metabolic disorders | |
| EP0536400A1 (de) | Tetrazolderivat und arzneimittel | |
| KR100280614B1 (ko) | 피페리딘 유도체 | |
| US6881736B1 (en) | Vitronectin receptor antagonists | |
| EP0765323A1 (de) | 4-(6-fluor-1,2-benzisoxazolyl)-1-piperidinyl-propoxy-chromen-4-one-derivate,ihre herstellung und ihre anwendung in der behandlung von psychosen, schizophrenie und angstzuständen | |
| JPH05112559A (ja) | ４−アミノ−５−ピリミジンカルボン酸誘導体 | |
| DK174366B1 (da) | 2-(substitueret methyl) -3-alkyl-4-(substitueret ethoxy)-pyridinforbindelser, farmaceutisk præparat, som indeholder en sådan, samt anvendelse af en sådan til fremstilling af et farmaceutisk præparat til behandling eller forebyggelse af mavesår |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: OTSUKA PHARMACEUTICAL COMPANY, LIMITED |