IL42799A - Carbazolic history of alcohols, sites and alkanoic acids, their preparation and pharmaceutical preparations containing signal - Google Patents
Carbazolic history of alcohols, sites and alkanoic acids, their preparation and pharmaceutical preparations containing signalInfo
- Publication number
- IL42799A IL42799A IL42799A IL4279973A IL42799A IL 42799 A IL42799 A IL 42799A IL 42799 A IL42799 A IL 42799A IL 4279973 A IL4279973 A IL 4279973A IL 42799 A IL42799 A IL 42799A
- Authority
- IL
- Israel
- Prior art keywords
- formula
- acetic acid
- chloro
- carbazole
- hydroxy
- Prior art date
Links
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title claims description 106
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 title claims description 79
- 238000002360 preparation method Methods 0.000 title claims description 46
- 239000002253 acid Substances 0.000 title claims description 43
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 title claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 98
- -1 nitro , amino Chemical group 0.000 claims description 78
- 125000003545 alkoxy group Chemical group 0.000 claims description 65
- 238000000034 method Methods 0.000 claims description 54
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 43
- 125000000217 alkyl group Chemical group 0.000 claims description 40
- 239000000203 mixture Substances 0.000 claims description 36
- 150000003839 salts Chemical group 0.000 claims description 35
- 239000001257 hydrogen Substances 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 238000004519 manufacturing process Methods 0.000 claims description 20
- 125000003282 alkyl amino group Chemical group 0.000 claims description 19
- 150000002148 esters Chemical class 0.000 claims description 19
- 150000001716 carbazoles Chemical class 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 17
- 150000002367 halogens Chemical group 0.000 claims description 17
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 15
- 239000007858 starting material Substances 0.000 claims description 15
- 150000002431 hydrogen Chemical group 0.000 claims description 14
- 125000001589 carboacyl group Chemical group 0.000 claims description 12
- QLQIYGDZYYQKGS-UHFFFAOYSA-N 2-(6-chloro-9h-carbazol-2-yl)propan-1-ol Chemical compound C1=C(Cl)C=C2C3=CC=C(C(CO)C)C=C3NC2=C1 QLQIYGDZYYQKGS-UHFFFAOYSA-N 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 150000007513 acids Chemical class 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- ONAAMJUFSFQSSD-UHFFFAOYSA-N 2-(6-chloro-9h-carbazol-2-yl)acetic acid Chemical compound C1=C(Cl)C=C2C3=CC=C(CC(=O)O)C=C3NC2=C1 ONAAMJUFSFQSSD-UHFFFAOYSA-N 0.000 claims description 5
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 5
- 230000000202 analgesic effect Effects 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- PZJKRCQOBPSLCF-UHFFFAOYSA-N 2-(6-chloro-9-methylcarbazol-1-yl)acetic acid Chemical compound ClC=1C=C2C=3C=CC=C(C3N(C2=CC1)C)CC(=O)O PZJKRCQOBPSLCF-UHFFFAOYSA-N 0.000 claims description 4
- 125000005153 alkyl sulfamoyl group Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000004494 ethyl ester group Chemical group 0.000 claims description 4
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 3
- 230000003356 anti-rheumatic effect Effects 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 241000282320 Panthera leo Species 0.000 claims 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 90
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 75
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 61
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 60
- 239000000243 solution Substances 0.000 description 55
- 239000011541 reaction mixture Substances 0.000 description 50
- 229960000583 acetic acid Drugs 0.000 description 44
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 38
- 238000010992 reflux Methods 0.000 description 36
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 26
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 25
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
- 238000001914 filtration Methods 0.000 description 23
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 18
- RYTWPAUCABOYJP-LURJTMIESA-N [(S)-3-oxocyclohexyl]acetic acid Chemical compound OC(=O)C[C@H]1CCCC(=O)C1 RYTWPAUCABOYJP-LURJTMIESA-N 0.000 description 15
- 239000012298 atmosphere Substances 0.000 description 14
- 239000002274 desiccant Substances 0.000 description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
- 239000002585 base Substances 0.000 description 13
- 229910052757 nitrogen Inorganic materials 0.000 description 13
- 238000001953 recrystallisation Methods 0.000 description 13
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 11
- 238000000605 extraction Methods 0.000 description 11
- 238000001704 evaporation Methods 0.000 description 10
- 230000008020 evaporation Effects 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 8
- 239000007789 gas Substances 0.000 description 8
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 8
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 8
- 239000005457 ice water Substances 0.000 description 8
- 241000699670 Mus sp. Species 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- 230000035484 reaction time Effects 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 6
- 230000008025 crystallization Effects 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 235000011181 potassium carbonates Nutrition 0.000 description 6
- 239000012258 stirred mixture Substances 0.000 description 6
- 206010030113 Oedema Diseases 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 239000012065 filter cake Substances 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- XKLNOVWDVMWTOB-UHFFFAOYSA-N 2,3,4,9-tetrahydro-1h-carbazole Chemical compound N1C2=CC=CC=C2C2=C1CCCC2 XKLNOVWDVMWTOB-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 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 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- 239000002260 anti-inflammatory agent Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- HYYTZURTTBOOPV-UHFFFAOYSA-N ethyl 2-(6-chloro-9H-carbazol-1-yl)acetate Chemical compound C(C)OC(CC1=CC=CC=2C3=CC(=CC=C3NC12)Cl)=O HYYTZURTTBOOPV-UHFFFAOYSA-N 0.000 description 4
- HAGBBNHRZNDPGE-UHFFFAOYSA-N ethyl 2-(6-chloro-9H-carbazol-4-yl)acetate Chemical compound C(C)OC(CC1=CC=CC=2NC3=CC=C(C=C3C12)Cl)=O HAGBBNHRZNDPGE-UHFFFAOYSA-N 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 235000015497 potassium bicarbonate Nutrition 0.000 description 4
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 4
- 239000011736 potassium bicarbonate Substances 0.000 description 4
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- YMJSQPNVQRHZDW-UHFFFAOYSA-N (3,4-dichlorophenyl)hydrazine Chemical compound NNC1=CC=C(Cl)C(Cl)=C1 YMJSQPNVQRHZDW-UHFFFAOYSA-N 0.000 description 3
- GFPJLZASIVURDY-UHFFFAOYSA-N (3-chlorophenyl)hydrazine Chemical compound NNC1=CC=CC(Cl)=C1 GFPJLZASIVURDY-UHFFFAOYSA-N 0.000 description 3
- RRNWXJAWRPITPU-UHFFFAOYSA-N 1-(4-chlorophenyl)-1-methylhydrazine Chemical group CN(N)C1=CC=C(Cl)C=C1 RRNWXJAWRPITPU-UHFFFAOYSA-N 0.000 description 3
- RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical class CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 description 3
- VECSVKNSAACGIB-UHFFFAOYSA-N 2-(6-chloro-9H-carbazol-1-yl)acetic acid Chemical compound ClC=1C=C2C=3C=CC=C(C3NC2=CC1)CC(=O)O VECSVKNSAACGIB-UHFFFAOYSA-N 0.000 description 3
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 241001465754 Metazoa Species 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 3
- 150000001350 alkyl halides Chemical class 0.000 description 3
- 239000000730 antalgic agent Substances 0.000 description 3
- 239000003435 antirheumatic agent Substances 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000012259 ether extract Substances 0.000 description 3
- LFXNTVMSOCUYIA-UHFFFAOYSA-N ethyl 2-(6-acetamido-9H-carbazol-2-yl)acetate Chemical compound C(C)OC(CC1=CC=2NC3=CC=C(C=C3C2C=C1)NC(C)=O)=O LFXNTVMSOCUYIA-UHFFFAOYSA-N 0.000 description 3
- SIHRKOZKOVXKFN-UHFFFAOYSA-N ethyl 2-(6-chloro-9H-carbazol-2-yl)acetate Chemical compound C(C)OC(CC1=CC=2NC3=CC=C(C=C3C2C=C1)Cl)=O SIHRKOZKOVXKFN-UHFFFAOYSA-N 0.000 description 3
- PFWOCVIKINICHM-UHFFFAOYSA-N ethyl 2-(6-methyl-9H-carbazol-2-yl)acetate Chemical compound C(C)OC(CC1=CC=2NC3=CC=C(C=C3C2C=C1)C)=O PFWOCVIKINICHM-UHFFFAOYSA-N 0.000 description 3
- WAWHBEPXRFDTLT-UHFFFAOYSA-N ethyl 2-(6-nitro-9H-carbazol-2-yl)acetate Chemical compound C(C)OC(CC1=CC=2NC3=CC=C(C=C3C2C=C1)[N+](=O)[O-])=O WAWHBEPXRFDTLT-UHFFFAOYSA-N 0.000 description 3
- NEYIEHVTWMKNCP-UHFFFAOYSA-N ethyl 2-(7-chloro-9H-carbazol-2-yl)acetate Chemical compound C(C)OC(CC1=CC=2NC3=CC(=CC=C3C2C=C1)Cl)=O NEYIEHVTWMKNCP-UHFFFAOYSA-N 0.000 description 3
- VPQFGSDQRACDFA-UHFFFAOYSA-N ethyl 2-(8-chloro-9H-carbazol-2-yl)acetate Chemical compound C(C)OC(CC1=CC=2NC3=C(C=CC=C3C2C=C1)Cl)=O VPQFGSDQRACDFA-UHFFFAOYSA-N 0.000 description 3
- VGVYUQRMNJWFEF-UHFFFAOYSA-N ethyl 3-(6-chloro-9H-carbazol-2-yl)propanoate Chemical compound C(C)OC(CCC1=CC=2NC3=CC=C(C=C3C2C=C1)Cl)=O VGVYUQRMNJWFEF-UHFFFAOYSA-N 0.000 description 3
- 210000002683 foot Anatomy 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 3
- 229940067157 phenylhydrazine Drugs 0.000 description 3
- 238000007363 ring formation reaction Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000006228 supernatant Substances 0.000 description 3
- 239000000829 suppository Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- HPIALSXRVQRGMK-UHFFFAOYSA-N (2,3-dichlorophenyl)hydrazine Chemical compound NNC1=CC=CC(Cl)=C1Cl HPIALSXRVQRGMK-UHFFFAOYSA-N 0.000 description 2
- NRESDXFFSNBDGP-UHFFFAOYSA-N (4-bromophenyl)hydrazine Chemical compound NNC1=CC=C(Br)C=C1 NRESDXFFSNBDGP-UHFFFAOYSA-N 0.000 description 2
- ZXBMIRYQUFQQNX-UHFFFAOYSA-N (4-fluorophenyl)hydrazine Chemical compound NNC1=CC=C(F)C=C1 ZXBMIRYQUFQQNX-UHFFFAOYSA-N 0.000 description 2
- PVRSIFAEUCUJPK-UHFFFAOYSA-N (4-methoxyphenyl)hydrazine Chemical compound COC1=CC=C(NN)C=C1 PVRSIFAEUCUJPK-UHFFFAOYSA-N 0.000 description 2
- XAMBIJWZVIZZOG-UHFFFAOYSA-N (4-methylphenyl)hydrazine Chemical compound CC1=CC=C(NN)C=C1 XAMBIJWZVIZZOG-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 2
- ZBGNQKQMJHXXRQ-UHFFFAOYSA-N 2-(3-oxocyclohexyl)propanoic acid Chemical compound OC(=O)C(C)C1CCCC(=O)C1 ZBGNQKQMJHXXRQ-UHFFFAOYSA-N 0.000 description 2
- UIUNPBLAXOCPDZ-UHFFFAOYSA-N 2-(6-bromo-9h-carbazol-2-yl)acetic acid Chemical compound C1=C(Br)C=C2C3=CC=C(CC(=O)O)C=C3NC2=C1 UIUNPBLAXOCPDZ-UHFFFAOYSA-N 0.000 description 2
- TVFXKUFKUMERQL-UHFFFAOYSA-N 2-(6-chloro-9H-carbazol-3-yl)acetic acid Chemical compound ClC=1C=C2C=3C=C(C=CC3NC2=CC1)CC(=O)O TVFXKUFKUMERQL-UHFFFAOYSA-N 0.000 description 2
- XIIFTYWLQJSAGM-UHFFFAOYSA-N 2-(6-chloro-9H-carbazol-4-yl)acetic acid Chemical compound ClC=1C=C2C=3C(=CC=CC3NC2=CC1)CC(=O)O XIIFTYWLQJSAGM-UHFFFAOYSA-N 0.000 description 2
- VHPURBXYUSMXHK-UHFFFAOYSA-N 2-(6-hydroxy-9H-carbazol-2-yl)acetic acid Chemical compound OC=1C=C2C=3C=CC(=CC3NC2=CC1)CC(=O)O VHPURBXYUSMXHK-UHFFFAOYSA-N 0.000 description 2
- XNPJDOFRBWXAEM-UHFFFAOYSA-N 2-(6-methoxy-9H-carbazol-2-yl)acetic acid Chemical compound COC=1C=C2C=3C=CC(=CC3NC2=CC1)CC(=O)O XNPJDOFRBWXAEM-UHFFFAOYSA-N 0.000 description 2
- XVIUJYDGUZGBTR-UHFFFAOYSA-N 2-(6-methyl-9H-carbazol-2-yl)acetic acid Chemical compound CC=1C=C2C=3C=CC(=CC3NC2=CC1)CC(=O)O XVIUJYDGUZGBTR-UHFFFAOYSA-N 0.000 description 2
- ZHLYCWPDXFIFKD-UHFFFAOYSA-N 2-(6-methylsulfanyl-2,3,4,9-tetrahydro-1H-carbazol-2-yl)acetic acid Chemical compound CSC=1C=C2C=3CCC(CC3NC2=CC1)CC(=O)O ZHLYCWPDXFIFKD-UHFFFAOYSA-N 0.000 description 2
- ZEGDKCCJFIJLFX-UHFFFAOYSA-N 2-(6-nitro-9H-carbazol-2-yl)acetic acid Chemical compound [N+](=O)([O-])C=1C=C2C=3C=CC(=CC3NC2=CC1)CC(=O)O ZEGDKCCJFIJLFX-UHFFFAOYSA-N 0.000 description 2
- DMCQBDWRSFYWAV-UHFFFAOYSA-N 2-(7-chloro-9H-carbazol-2-yl)acetic acid Chemical compound ClC1=CC=C2C=3C=CC(=CC3NC2=C1)CC(=O)O DMCQBDWRSFYWAV-UHFFFAOYSA-N 0.000 description 2
- ODGAQUIHAIDCMY-UHFFFAOYSA-N 2-(7-chloro-9H-carbazol-3-yl)acetic acid Chemical compound ClC1=CC=C2C=3C=C(C=CC3NC2=C1)CC(=O)O ODGAQUIHAIDCMY-UHFFFAOYSA-N 0.000 description 2
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- 229910000464 lead oxide Inorganic materials 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- ZDGGJQMSELMHLK-UHFFFAOYSA-N m-Trifluoromethylhippuric acid Chemical compound OC(=O)CNC(=O)C1=CC=CC(C(F)(F)F)=C1 ZDGGJQMSELMHLK-UHFFFAOYSA-N 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 229960002216 methylparaben Drugs 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- IGCOGQZYAPWSGX-UHFFFAOYSA-N n-(4-hydrazinylphenyl)acetamide Chemical group CC(=O)NC1=CC=C(NN)C=C1 IGCOGQZYAPWSGX-UHFFFAOYSA-N 0.000 description 1
- JWFQIJOWFMAEMA-UHFFFAOYSA-N n-(9h-carbazol-3-yl)acetamide Chemical group C1=CC=C2C3=CC(NC(=O)C)=CC=C3NC2=C1 JWFQIJOWFMAEMA-UHFFFAOYSA-N 0.000 description 1
- ZBUQPAJRQXISTC-UHFFFAOYSA-N n-(chloromethyl)-n-ethylethanamine Chemical compound CCN(CC)CCl ZBUQPAJRQXISTC-UHFFFAOYSA-N 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
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- YEXPOXQUZXUXJW-UHFFFAOYSA-N oxolead Chemical compound [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229960002895 phenylbutazone Drugs 0.000 description 1
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000003755 preservative agent Substances 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
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000010956 selective crystallization Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 230000001562 ulcerogenic effect Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
-
- 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
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pain & Pain Management (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US27414272A | 1972-07-24 | 1972-07-24 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL42799A0 IL42799A0 (en) | 1973-10-25 |
| IL42799A true IL42799A (en) | 1977-03-31 |
Family
ID=23046965
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL42799A IL42799A (en) | 1972-07-24 | 1973-07-20 | Carbazolic history of alcohols, sites and alkanoic acids, their preparation and pharmaceutical preparations containing signal |
Country Status (26)
| Country | Link |
|---|---|
| JP (1) | JPS5740144B2 (en, 2012) |
| KR (1) | KR780000289B1 (en, 2012) |
| AR (1) | AR205331A1 (en, 2012) |
| AT (1) | AT325607B (en, 2012) |
| AU (1) | AU475534B2 (en, 2012) |
| BE (1) | BE802596A (en, 2012) |
| CA (1) | CA1026348A (en, 2012) |
| CH (1) | CH587819A5 (en, 2012) |
| DD (1) | DD107681A5 (en, 2012) |
| DE (1) | DE2337340C2 (en, 2012) |
| DK (1) | DK138537B (en, 2012) |
| FI (1) | FI59244C (en, 2012) |
| FR (1) | FR2193611B1 (en, 2012) |
| GB (1) | GB1385620A (en, 2012) |
| HK (1) | HK49878A (en, 2012) |
| HU (1) | HU167611B (en, 2012) |
| IE (1) | IE37942B1 (en, 2012) |
| IL (1) | IL42799A (en, 2012) |
| KE (1) | KE2847A (en, 2012) |
| LU (1) | LU68071A1 (en, 2012) |
| MY (1) | MY7800315A (en, 2012) |
| NL (1) | NL169877C (en, 2012) |
| NO (1) | NO142865C (en, 2012) |
| SE (2) | SE402283B (en, 2012) |
| SU (1) | SU509220A3 (en, 2012) |
| ZA (1) | ZA734047B (en, 2012) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4146542A (en) * | 1978-06-12 | 1979-03-27 | Hoffmann-La Roche Inc. | Dihydrocarbazole acetic acid and esters thereof |
| US4150031A (en) * | 1978-06-26 | 1979-04-17 | Hoffmann-La Roche Inc. | Hydroxy methyl carbazole acetic acid and esters |
| US4158007A (en) * | 1978-08-21 | 1979-06-12 | Hoffmann-La Roche Inc. | Carbazole methyl malonates |
| US4501908A (en) * | 1981-03-12 | 1985-02-26 | Hoffmann-La Roche Inc. | 2,3-Isopropylidene ribonic acid, 1,4-lactones |
| JPS6040256U (ja) * | 1983-08-25 | 1985-03-20 | 伊東 璋 | 容器類洗浄機 |
| DE3768097D1 (de) * | 1986-01-23 | 1991-04-04 | Merck Frosst Canada Inc | Tetrahydrocarbazol-1-alkansaeuren. |
| DE3786030T2 (de) | 1986-03-27 | 1993-12-02 | Merck Frosst Canada Inc | Tetrahydrocarbazole Ester. |
| CA1326030C (en) * | 1987-07-21 | 1994-01-11 | John W. Gillard | Cyclohept[b]indolealkanoic acids |
| EP0307077A1 (en) * | 1987-07-21 | 1989-03-15 | Merck Frosst Canada Inc. | Tetrahydrocarbazoles for the improvement of cyclosporin therapy |
| PT95692A (pt) * | 1989-10-27 | 1991-09-13 | American Home Prod | Processo para a preparacao de derivados de acidos indole-,indeno-,piranoindole- e tetra-hidrocarbazole-alcanoicos, ou quais sao uteis como inibidores de pla2 e da lipoxigenase |
| US6013808A (en) * | 1998-06-16 | 2000-01-11 | Pfizer Inc. | Method of purifying carbazole ester precursors of 6-chloro-α-methyl-carbazole-2-acetic acid |
| JP2004010601A (ja) * | 2002-06-11 | 2004-01-15 | Nippon Steel Chem Co Ltd | インドール誘導体の製造方法及びそのための有用な中間体 |
| CA2512704A1 (en) * | 2003-01-14 | 2004-08-05 | Merck & Co., Inc. | Geminally di-substituted nsaid derivatives as abeta 42 lowering agents |
| CA2524846C (en) * | 2003-05-06 | 2014-07-22 | Air Products And Chemicals, Inc. | Hydrogen storage reversible hydrogenated of pi-conjugated substrates |
| JP2007502251A (ja) * | 2003-08-15 | 2007-02-08 | ユニヴェルシテ・ラヴァル | ２位官能化及び２，７位二官能化カルバゾール類のモノマー類、オリゴマー類、及びポリマー類 |
| US7601856B2 (en) | 2006-07-27 | 2009-10-13 | Wyeth | Benzofurans as potassium ion channel modulators |
| US7662831B2 (en) | 2006-07-27 | 2010-02-16 | Wyeth Llc | Tetracyclic indoles as potassium channel modulators |
| PL2802320T3 (pl) * | 2011-11-15 | 2019-09-30 | Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd. | Związki tricykliczne, zawierające je kompozycje i ich zastosowania |
| JP5940036B2 (ja) * | 2013-10-08 | 2016-06-29 | テックフィールズ バイオケム カンパニー リミテッド | 非常に速い皮膚透過率を有するアリール−及びヘテロアリールプロピオン酸の正荷電水溶性プロドラッグ |
| JPWO2021193708A1 (en, 2012) * | 2020-03-25 | 2021-09-30 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD70880A (en, 2012) * | ||||
| US3580926A (en) * | 1969-11-10 | 1971-05-25 | Parke Davis & Co | Carbazole-4-alkanoic acids and tetrahydrocarbazole-4-alkanoic acids |
| ZA715217B (en) * | 1970-08-20 | 1972-04-26 | Org Nv | Anti-inflammatory preparations |
-
1973
- 1973-01-01 AR AR249230A patent/AR205331A1/es active
- 1973-06-14 ZA ZA734047A patent/ZA734047B/xx unknown
- 1973-06-15 CH CH871673A patent/CH587819A5/xx not_active IP Right Cessation
- 1973-07-20 IL IL42799A patent/IL42799A/en unknown
- 1973-07-20 HU HUHO1597A patent/HU167611B/hu unknown
- 1973-07-20 KR KR7301174A patent/KR780000289B1/ko not_active Expired
- 1973-07-20 BE BE133691A patent/BE802596A/xx not_active IP Right Cessation
- 1973-07-23 DD DD172456A patent/DD107681A5/xx unknown
- 1973-07-23 IE IE1252/73A patent/IE37942B1/xx unknown
- 1973-07-23 FI FI2311/73A patent/FI59244C/fi active
- 1973-07-23 SE SE7310244A patent/SE402283B/xx unknown
- 1973-07-23 AU AU58390/73A patent/AU475534B2/en not_active Expired
- 1973-07-23 LU LU68071A patent/LU68071A1/xx unknown
- 1973-07-23 AT AT649773A patent/AT325607B/de not_active IP Right Cessation
- 1973-07-23 NO NO2975/73A patent/NO142865C/no unknown
- 1973-07-23 CA CA177,061A patent/CA1026348A/en not_active Expired
- 1973-07-23 DE DE2337340A patent/DE2337340C2/de not_active Expired
- 1973-07-23 GB GB3496873A patent/GB1385620A/en not_active Expired
- 1973-07-23 DK DK405973AA patent/DK138537B/da not_active IP Right Cessation
- 1973-07-23 JP JP48081008A patent/JPS5740144B2/ja not_active Expired
- 1973-07-24 NL NLAANVRAGE7310275,A patent/NL169877C/xx not_active IP Right Cessation
- 1973-07-24 FR FR7327020A patent/FR2193611B1/fr not_active Expired
- 1973-07-24 SU SU1950151A patent/SU509220A3/ru active
-
1976
- 1976-05-21 SE SE7605813A patent/SE7605813L/xx unknown
-
1978
- 1978-06-13 KE KE2847A patent/KE2847A/xx unknown
- 1978-08-31 HK HK498/78A patent/HK49878A/xx unknown
- 1978-12-30 MY MY315/78A patent/MY7800315A/xx unknown
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