ZA200204199B - Substituted pyrrole mannich bases to combat pain and allergic reactions. - Google Patents
Substituted pyrrole mannich bases to combat pain and allergic reactions. Download PDFInfo
- Publication number
- ZA200204199B ZA200204199B ZA200204199A ZA200204199A ZA200204199B ZA 200204199 B ZA200204199 B ZA 200204199B ZA 200204199 A ZA200204199 A ZA 200204199A ZA 200204199 A ZA200204199 A ZA 200204199A ZA 200204199 B ZA200204199 B ZA 200204199B
- Authority
- ZA
- South Africa
- Prior art keywords
- phenyl
- radical
- aryl
- methyl
- pyrrol
- Prior art date
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- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 title claims description 77
- RREANTFLPGEWEN-MBLPBCRHSA-N 7-[4-[[(3z)-3-[4-amino-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidin-2-yl]imino-5-fluoro-2-oxoindol-1-yl]methyl]piperazin-1-yl]-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(\N=C/3C4=CC(F)=CC=C4N(CN4CCN(CC4)C=4C(=CC=5C(=O)C(C(O)=O)=CN(C=5C=4)C4CC4)F)C\3=O)=NC=2)N)=C1 RREANTFLPGEWEN-MBLPBCRHSA-N 0.000 title claims description 51
- 150000003233 pyrroles Chemical class 0.000 title claims description 49
- 208000002193 Pain Diseases 0.000 title claims description 19
- 230000036407 pain Effects 0.000 title claims description 14
- 206010020751 Hypersensitivity Diseases 0.000 title claims description 7
- -1 heteroaryl radical Chemical class 0.000 claims description 159
- 150000003254 radicals Chemical group 0.000 claims description 83
- 125000003118 aryl group Chemical group 0.000 claims description 68
- 238000002360 preparation method Methods 0.000 claims description 58
- 239000003814 drug Substances 0.000 claims description 45
- 150000005840 aryl radicals Chemical group 0.000 claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 29
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 20
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 20
- 238000011282 treatment Methods 0.000 claims description 19
- 229910052794 bromium Inorganic materials 0.000 claims description 17
- 229910052801 chlorine Inorganic materials 0.000 claims description 17
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 14
- 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 claims description 13
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims description 13
- 239000012346 acetyl chloride Substances 0.000 claims description 13
- 229910052731 fluorine Inorganic materials 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 11
- 150000007975 iminium salts Chemical class 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 8
- ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 7
- 238000000746 purification Methods 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 6
- 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 claims description 6
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 6
- 208000007848 Alcoholism Diseases 0.000 claims description 6
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 6
- 206010012735 Diarrhoea Diseases 0.000 claims description 6
- 206010013654 Drug abuse Diseases 0.000 claims description 6
- 208000007882 Gastritis Diseases 0.000 claims description 6
- 206010061218 Inflammation Diseases 0.000 claims description 6
- 208000025865 Ulcer Diseases 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 206010001584 alcohol abuse Diseases 0.000 claims description 6
- 208000025746 alcohol use disease Diseases 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 150000003335 secondary amines Chemical class 0.000 claims description 6
- 208000011117 substance-related disease Diseases 0.000 claims description 6
- 231100000397 ulcer Toxicity 0.000 claims description 6
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 5
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 5
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 5
- 208000032841 Bulimia Diseases 0.000 claims description 5
- 206010006550 Bulimia nervosa Diseases 0.000 claims description 5
- 208000009132 Catalepsy Diseases 0.000 claims description 5
- 208000000094 Chronic Pain Diseases 0.000 claims description 5
- 208000010412 Glaucoma Diseases 0.000 claims description 5
- 208000019695 Migraine disease Diseases 0.000 claims description 5
- 206010046543 Urinary incontinence Diseases 0.000 claims description 5
- 206010047853 Waxy flexibility Diseases 0.000 claims description 5
- 208000022531 anorexia Diseases 0.000 claims description 5
- 208000006673 asthma Diseases 0.000 claims description 5
- 206010061428 decreased appetite Diseases 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- 201000003631 narcolepsy Diseases 0.000 claims description 5
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 5
- 230000035939 shock Effects 0.000 claims description 5
- 125000001617 2,3-dimethoxy phenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 4
- 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 4
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 4
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 4
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 4
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 4
- JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 claims description 4
- 230000004054 inflammatory process Effects 0.000 claims description 4
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 4
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 229930192474 thiophene Natural products 0.000 claims description 4
- 238000005406 washing Methods 0.000 claims description 4
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 3
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 3
- KRTGJZMJJVEKRX-UHFFFAOYSA-N 2-phenylethan-1-yl Chemical compound [CH2]CC1=CC=CC=C1 KRTGJZMJJVEKRX-UHFFFAOYSA-N 0.000 claims description 3
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 3
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims description 3
- 125000001207 fluorophenyl group Chemical group 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
- VLRLJQCSYSRMRI-UHFFFAOYSA-N 1-(1-tert-butylpyrrol-2-yl)-n,n-dimethyl-1-phenylmethanamine Chemical compound C=1C=CC=CC=1C(N(C)C)C1=CC=CN1C(C)(C)C VLRLJQCSYSRMRI-UHFFFAOYSA-N 0.000 claims description 2
- JADQMNMEFKANIU-UHFFFAOYSA-N 1-[(4-fluorophenyl)-(1-methylpyrrol-2-yl)methyl]piperidine Chemical compound CN1C=CC=C1C(C=1C=CC(F)=CC=1)N1CCCCC1 JADQMNMEFKANIU-UHFFFAOYSA-N 0.000 claims description 2
- WPXFORGQVXJJSX-UHFFFAOYSA-N 1-[[1-(2-chloroethyl)pyrrol-2-yl]-(4-fluorophenyl)methyl]piperidine Chemical compound C1=CC(F)=CC=C1C(C=1N(C=CC=1)CCCl)N1CCCCC1 WPXFORGQVXJJSX-UHFFFAOYSA-N 0.000 claims description 2
- JVOHDBDCNZTAKA-UHFFFAOYSA-N 1-[[1-(furan-2-yl)pyrrol-2-yl]-(2-methoxyphenyl)methyl]piperidine Chemical compound COC1=CC=CC=C1C(C=1N(C=CC=1)C=1OC=CC=1)N1CCCCC1 JVOHDBDCNZTAKA-UHFFFAOYSA-N 0.000 claims description 2
- KMDBGXVNNGHXHN-UHFFFAOYSA-N 2-[2-[(2-methoxyphenyl)-pyrrolidin-1-ylmethyl]pyrrol-1-yl]benzenecarbothioamide Chemical compound COC1=CC=CC=C1C(C=1N(C=CC=1)C=1C(=CC=CC=1)C(N)=S)N1CCCC1 KMDBGXVNNGHXHN-UHFFFAOYSA-N 0.000 claims description 2
- GJJPMTKDLWCEIC-UHFFFAOYSA-N 2-[2-[(2-methylphenyl)-pyrrolidin-1-ylmethyl]pyrrol-1-yl]aniline Chemical compound CC1=CC=CC=C1C(C=1N(C=CC=1)C=1C(=CC=CC=1)N)N1CCCC1 GJJPMTKDLWCEIC-UHFFFAOYSA-N 0.000 claims description 2
- UDBHUYSLCGJCOP-UHFFFAOYSA-N 2-[2-[dimethylamino(phenyl)methyl]pyrrol-1-yl]aniline Chemical compound C=1C=CC=CC=1C(N(C)C)C1=CC=CN1C1=CC=CC=C1N UDBHUYSLCGJCOP-UHFFFAOYSA-N 0.000 claims description 2
- ZRVAEMSMNZULHI-UHFFFAOYSA-N 2-[[2-[(3-bromo-4-fluorophenyl)-pyrrolidin-1-ylmethyl]pyrrol-1-yl]methyl]pyridine Chemical compound C1=C(Br)C(F)=CC=C1C(C=1N(C=CC=1)CC=1N=CC=CC=1)N1CCCC1 ZRVAEMSMNZULHI-UHFFFAOYSA-N 0.000 claims description 2
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- 238000007796 conventional method Methods 0.000 claims description 2
- 125000004188 dichlorophenyl group Chemical group 0.000 claims description 2
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- AZQDHQDXEFBCPW-UHFFFAOYSA-N BrC=1C=C(C=CC1)C(C=1N(C=CC1)CC1=NC=CC=C1)N1CCCC1.ClC1=C(C(=CC=C1)F)C(C=1N(C=CC1)C1=C(C=CC=C1)N)N1CCCC1 Chemical compound BrC=1C=C(C=CC1)C(C=1N(C=CC1)CC1=NC=CC=C1)N1CCCC1.ClC1=C(C(=CC=C1)F)C(C=1N(C=CC1)C1=C(C=CC=C1)N)N1CCCC1 AZQDHQDXEFBCPW-UHFFFAOYSA-N 0.000 claims 1
- UTORPQLCVSWPPY-UHFFFAOYSA-N C1(=CC=CC=C1)C(C=1N(C=CC1)C1=C(C(=S)N)C=CC=C1)N1CCCC1.CN(C)C(C=1N(C=CC1)C1=C(C(=S)N)C=CC=C1)C1=C(C=CC=C1)C Chemical compound C1(=CC=CC=C1)C(C=1N(C=CC1)C1=C(C(=S)N)C=CC=C1)N1CCCC1.CN(C)C(C=1N(C=CC1)C1=C(C(=S)N)C=CC=C1)C1=C(C=CC=C1)C UTORPQLCVSWPPY-UHFFFAOYSA-N 0.000 claims 1
- PBMHPMNOEQDAFV-UHFFFAOYSA-N CN(C(C=1N(C=CC1)C1=CC=CC=C1)C1=CC=CC=C1)C.CN(C)C(C=1N(C=CC1)CCC#N)C1=C(C=CC=C1)OC.C(C)N1C(=CC=C1)C(C1=C(C=CC=C1)OC)N(C)C Chemical compound CN(C(C=1N(C=CC1)C1=CC=CC=C1)C1=CC=CC=C1)C.CN(C)C(C=1N(C=CC1)CCC#N)C1=C(C=CC=C1)OC.C(C)N1C(=CC=C1)C(C1=C(C=CC=C1)OC)N(C)C PBMHPMNOEQDAFV-UHFFFAOYSA-N 0.000 claims 1
- WULDVSUGPRYDDY-UHFFFAOYSA-N N1=C(C=CC=C1)CN1C(=CC=C1)C(C1=CC=C(C#N)C=C1)N1CCCC1.ClC1=C(C(=CC=C1)F)C(C=1N(C=CC1)CC1=NC=CC=C1)N1CCCC1 Chemical compound N1=C(C=CC=C1)CN1C(=CC=C1)C(C1=CC=C(C#N)C=C1)N1CCCC1.ClC1=C(C(=CC=C1)F)C(C=1N(C=CC1)CC1=NC=CC=C1)N1CCCC1 WULDVSUGPRYDDY-UHFFFAOYSA-N 0.000 claims 1
- QIOZLISABUUKJY-UHFFFAOYSA-N Thiobenzamide Chemical compound NC(=S)C1=CC=CC=C1 QIOZLISABUUKJY-UHFFFAOYSA-N 0.000 claims 1
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- 125000003944 tolyl group Chemical group 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 description 80
- 238000003786 synthesis reaction Methods 0.000 description 78
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 42
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 37
- 238000006243 chemical reaction Methods 0.000 description 36
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 31
- 238000012512 characterization method Methods 0.000 description 21
- 239000000243 solution Substances 0.000 description 18
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- XKVPIXHOPCPNMV-UHFFFAOYSA-N 2-methyl-4-pyrrol-1-ylpyridine Chemical compound C1=NC(C)=CC(N2C=CC=C2)=C1 XKVPIXHOPCPNMV-UHFFFAOYSA-N 0.000 description 7
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- 238000011835 investigation Methods 0.000 description 7
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- RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 description 5
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- 125000002947 alkylene group Chemical group 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
- YJLIMDZTOBBHOI-UHFFFAOYSA-M dimethyl-[(2-methylphenyl)methylidene]azanium;chloride Chemical compound [Cl-].CC1=CC=CC=C1C=[N+](C)C YJLIMDZTOBBHOI-UHFFFAOYSA-M 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
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- 239000004220 glutamic acid Substances 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- OVWYEQOVUDKZNU-UHFFFAOYSA-N m-tolualdehyde Chemical compound CC1=CC=CC(C=O)=C1 OVWYEQOVUDKZNU-UHFFFAOYSA-N 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 210000001767 medulla oblongata Anatomy 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 229960005181 morphine Drugs 0.000 description 1
- 210000004400 mucous membrane Anatomy 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
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 239000002245 particle Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 230000036280 sedation Effects 0.000 description 1
- 230000020341 sensory perception of pain Effects 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 210000003568 synaptosome Anatomy 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 229960003107 tramadol hydrochloride 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
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/335—Radicals substituted by nitrogen atoms not forming part of a nitro radical
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- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P3/04—Anorexiants; Antiobesity agents
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Pulmonology (AREA)
- Pain & Pain Management (AREA)
- Addiction (AREA)
- Urology & Nephrology (AREA)
- Psychiatry (AREA)
- Diabetes (AREA)
- Ophthalmology & Optometry (AREA)
- Hematology (AREA)
- Immunology (AREA)
- Obesity (AREA)
- Anesthesiology (AREA)
- Cardiology (AREA)
- Rheumatology (AREA)
- Child & Adolescent Psychology (AREA)
- Psychology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19963174A DE19963174A1 (de) | 1999-12-27 | 1999-12-27 | Substituierte Pyrrol-Mannichbasen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200204199B true ZA200204199B (en) | 2004-02-10 |
Family
ID=7934619
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200204199A ZA200204199B (en) | 1999-12-27 | 2002-05-27 | Substituted pyrrole mannich bases to combat pain and allergic reactions. |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US7034018B2 (da) |
| EP (1) | EP1246799B1 (da) |
| JP (1) | JP2003527350A (da) |
| KR (1) | KR20020067571A (da) |
| CN (1) | CN1247542C (da) |
| AR (1) | AR027058A1 (da) |
| AT (1) | ATE252077T1 (da) |
| AU (1) | AU782909B2 (da) |
| BR (1) | BR0016814A (da) |
| CA (1) | CA2396502A1 (da) |
| CO (1) | CO5261489A1 (da) |
| CZ (1) | CZ20022239A3 (da) |
| DE (2) | DE19963174A1 (da) |
| DK (1) | DK1246799T3 (da) |
| ES (1) | ES2208466T3 (da) |
| HK (1) | HK1051855A1 (da) |
| HU (1) | HUP0203695A3 (da) |
| IL (2) | IL149811A0 (da) |
| MX (1) | MXPA02005793A (da) |
| NO (1) | NO20023028L (da) |
| NZ (1) | NZ519975A (da) |
| PE (1) | PE20010988A1 (da) |
| PL (1) | PL355413A1 (da) |
| PT (1) | PT1246799E (da) |
| RU (1) | RU2002120468A (da) |
| SK (1) | SK286274B6 (da) |
| TR (1) | TR200302178T4 (da) |
| WO (1) | WO2001047878A1 (da) |
| ZA (1) | ZA200204199B (da) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0016453D0 (en) * | 2000-07-04 | 2000-08-23 | Hoffmann La Roche | Pyrrole derivatives |
| CA2473461C (en) * | 2002-01-11 | 2011-11-01 | Sankyo Company, Limited | Amino alcohol derivative or phosphonic acid derivative and medicinal composition containing these |
| DE10261130A1 (de) * | 2002-12-20 | 2004-07-01 | Grünenthal GmbH | Arzneimittel enthaltend substituierte 2,5-Diaminomethyl-1H-pyrrole |
| AU2005304267A1 (en) * | 2004-11-09 | 2006-05-18 | Aurora Electric (Holdings) Pty. Limited | Air driven fan generator system |
| CN102221678A (zh) * | 2011-05-17 | 2011-10-19 | 重庆长安汽车股份有限公司 | 一种电池系统在线寿命计算方法 |
| TW201416348A (zh) * | 2012-08-29 | 2014-05-01 | Gruenenthal Chemie | 以氟甲基取代之吡咯甲醯胺 |
| KR102084185B1 (ko) * | 2013-08-29 | 2020-03-04 | 주식회사 대웅제약 | 테트라히드로사이클로펜타피롤 유도체 및 이의 제조방법 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4341402A (en) * | 1980-03-06 | 1982-07-27 | Sterling Drug Inc. | Systems employing indole color formers |
| US4335136A (en) | 1980-04-18 | 1982-06-15 | E. I. Du Pont De Nemours And Company | Anti-inflammatory 4,5-diaryl-α-(polyfluoroalkyl)-1H-pyrrole-2-methanamines |
| JPH07509705A (ja) * | 1992-08-06 | 1995-10-26 | スミスクライン・ビーチャム・パブリック・リミテッド・カンパニー | ドーパミンｄ３レセプター拮抗薬用５−（２−オキシフェニル）−ピロール誘導体 |
| GB9325827D0 (en) * | 1993-12-17 | 1994-02-23 | Smithkline Beecham Plc | Compounds |
| ES2208964T3 (es) * | 1996-12-10 | 2004-06-16 | G.D. SEARLE & CO. | Compuestos de pirrolilo substituidos para el tratamiento de la inflamacion. |
-
1999
- 1999-12-27 DE DE19963174A patent/DE19963174A1/de not_active Ceased
-
2000
- 2000-12-20 ES ES00991220T patent/ES2208466T3/es not_active Expired - Lifetime
- 2000-12-20 PT PT00991220T patent/PT1246799E/pt unknown
- 2000-12-20 DE DE50004114T patent/DE50004114D1/de not_active Expired - Lifetime
- 2000-12-20 AT AT00991220T patent/ATE252077T1/de active
- 2000-12-20 KR KR1020027008185A patent/KR20020067571A/ko not_active Application Discontinuation
- 2000-12-20 BR BR0016814-9A patent/BR0016814A/pt not_active Application Discontinuation
- 2000-12-20 DK DK00991220T patent/DK1246799T3/da active
- 2000-12-20 IL IL14981100A patent/IL149811A0/xx active IP Right Grant
- 2000-12-20 RU RU2002120468/04A patent/RU2002120468A/ru unknown
- 2000-12-20 MX MXPA02005793A patent/MXPA02005793A/es active IP Right Grant
- 2000-12-20 PL PL00355413A patent/PL355413A1/xx unknown
- 2000-12-20 JP JP2001549351A patent/JP2003527350A/ja not_active Withdrawn
- 2000-12-20 AU AU31611/01A patent/AU782909B2/en not_active Ceased
- 2000-12-20 HU HU0203695A patent/HUP0203695A3/hu unknown
- 2000-12-20 US US10/168,964 patent/US7034018B2/en not_active Expired - Fee Related
- 2000-12-20 CZ CZ20022239A patent/CZ20022239A3/cs unknown
- 2000-12-20 SK SK730-2002A patent/SK286274B6/sk not_active IP Right Cessation
- 2000-12-20 CA CA002396502A patent/CA2396502A1/en not_active Abandoned
- 2000-12-20 EP EP00991220A patent/EP1246799B1/de not_active Expired - Lifetime
- 2000-12-20 TR TR2003/02178T patent/TR200302178T4/xx unknown
- 2000-12-20 CN CNB008178739A patent/CN1247542C/zh not_active Expired - Fee Related
- 2000-12-20 NZ NZ519975A patent/NZ519975A/en unknown
- 2000-12-20 WO PCT/EP2000/012976 patent/WO2001047878A1/de active Search and Examination
- 2000-12-21 AR ARP000106837A patent/AR027058A1/es unknown
- 2000-12-22 CO CO00097382A patent/CO5261489A1/es not_active Application Discontinuation
- 2000-12-26 PE PE2000001398A patent/PE20010988A1/es not_active Application Discontinuation
-
2002
- 2002-05-27 ZA ZA200204199A patent/ZA200204199B/en unknown
- 2002-06-21 NO NO20023028A patent/NO20023028L/no not_active Application Discontinuation
-
2003
- 2003-04-09 HK HK03102525A patent/HK1051855A1/xx not_active IP Right Cessation
-
2004
- 2004-01-01 IL IL149811A patent/IL149811A/en not_active IP Right Cessation
Also Published As
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| Publication | Publication Date | Title |
|---|---|---|
| US7091220B2 (en) | Substituted indole Mannich bases | |
| AU782909B2 (en) | Substituted pyrrole mannich bases to combat pain and allergic reactions | |
| US6774136B2 (en) | Substituted 1 and 2 naphthol mannich bases | |
| WO2001047882A2 (de) | Substanzbibliothek erhältlich durch die umsetzung von aldehyden mit sekundären aminen, säurechloriden und naphtol-, pyrrol- und/oder indolverbindungen |