HUP0303623A2 - Kondenzált piridinszármazékok, eljárás az előállításukra és ezeket tartalmazó gyógyászati készítmények vanilloid receptor antagonistaként fájdalom kezelésére - Google Patents
Kondenzált piridinszármazékok, eljárás az előállításukra és ezeket tartalmazó gyógyászati készítmények vanilloid receptor antagonistaként fájdalom kezelésére Download PDFInfo
- Publication number
- HUP0303623A2 HUP0303623A2 HU0303623A HUP0303623A HUP0303623A2 HU P0303623 A2 HUP0303623 A2 HU P0303623A2 HU 0303623 A HU0303623 A HU 0303623A HU P0303623 A HUP0303623 A HU P0303623A HU P0303623 A2 HUP0303623 A2 HU P0303623A2
- Authority
- HU
- Hungary
- Prior art keywords
- alkyl
- group
- phenyl
- substituted
- compound
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 17
- 208000002193 Pain Diseases 0.000 title claims abstract description 12
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- 230000008569 process Effects 0.000 title claims abstract description 5
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 7
- 230000036407 pain Effects 0.000 title abstract description 9
- 239000000085 vanilloid receptor antagonist Substances 0.000 title abstract description 8
- 150000003222 pyridines Chemical class 0.000 title abstract description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 96
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 43
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 41
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 38
- 150000003839 salts Chemical class 0.000 claims abstract description 36
- 238000011282 treatment Methods 0.000 claims abstract description 36
- 239000002253 acid Substances 0.000 claims abstract description 30
- 239000012458 free base Substances 0.000 claims abstract description 27
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 20
- -1 -OH Chemical group 0.000 claims abstract description 17
- 125000005843 halogen group Chemical group 0.000 claims abstract description 14
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 9
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 8
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims abstract description 7
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 7
- BJLUORNGPCXNHM-UHFFFAOYSA-N 1h-pyrido[3,2-d]pyrimidine-2,4-dione Chemical compound C1=CN=C2C(=O)NC(=O)NC2=C1 BJLUORNGPCXNHM-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 6
- 125000006277 halobenzyl group Chemical group 0.000 claims abstract description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 4
- 201000005569 Gout Diseases 0.000 claims abstract description 3
- 208000000491 Tendinopathy Diseases 0.000 claims abstract description 3
- 206010043255 Tendonitis Diseases 0.000 claims abstract description 3
- 201000004415 tendinitis Diseases 0.000 claims abstract description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 69
- 239000000203 mixture Substances 0.000 claims description 45
- 239000004480 active ingredient Substances 0.000 claims description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
- 102000011040 TRPV Cation Channels Human genes 0.000 claims description 12
- 108010062740 TRPV Cation Channels Proteins 0.000 claims description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 11
- 201000010099 disease Diseases 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 claims description 8
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims description 8
- BOBBYBHJYYJHHQ-UHFFFAOYSA-N 7-tert-butyl-6-(4-chlorophenyl)-2-sulfanylidene-1h-pyrido[2,3-d]pyrimidin-4-one Chemical compound CC(C)(C)C1=NC=2NC(=S)NC(=O)C=2C=C1C1=CC=C(Cl)C=C1 BOBBYBHJYYJHHQ-UHFFFAOYSA-N 0.000 claims description 7
- 230000002265 prevention Effects 0.000 claims description 7
- OGJSXKLSNLMPCL-UHFFFAOYSA-N 1-(4-chlorophenyl)-3,3-dimethylbutan-2-one Chemical compound CC(C)(C)C(=O)CC1=CC=C(Cl)C=C1 OGJSXKLSNLMPCL-UHFFFAOYSA-N 0.000 claims description 6
- YYASVUNKUYCHIU-UHFFFAOYSA-N 2-(4-chlorophenyl)-1-(dimethylamino)-4,4-dimethylpent-1-en-3-one Chemical compound CN(C)C=C(C(=O)C(C)(C)C)C1=CC=C(Cl)C=C1 YYASVUNKUYCHIU-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 230000004913 activation Effects 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 5
- 150000002431 hydrogen Chemical group 0.000 claims description 5
- 239000004201 L-cysteine Substances 0.000 claims description 4
- 235000013878 L-cysteine Nutrition 0.000 claims description 4
- NHDODQWIKUYWMW-UHFFFAOYSA-N 1-bromo-4-chlorobenzene Chemical compound ClC1=CC=C(Br)C=C1 NHDODQWIKUYWMW-UHFFFAOYSA-N 0.000 claims description 3
- BWYGMIYEADAIGW-UHFFFAOYSA-N 6-amino-2-sulfanylidene-1h-pyrimidin-4-one;hydrate Chemical compound O.NC1=CC(=O)NC(=S)N1 BWYGMIYEADAIGW-UHFFFAOYSA-N 0.000 claims description 3
- 208000000094 Chronic Pain Diseases 0.000 claims description 3
- 241000124008 Mammalia Species 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 201000008482 osteoarthritis Diseases 0.000 claims description 3
- 229910052763 palladium Inorganic materials 0.000 claims description 3
- PJGSXYOJTGTZAV-UHFFFAOYSA-N pinacolone Chemical compound CC(=O)C(C)(C)C PJGSXYOJTGTZAV-UHFFFAOYSA-N 0.000 claims description 3
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 3
- 230000001225 therapeutic effect Effects 0.000 claims description 3
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 2
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 claims description 2
- 235000019345 sodium thiosulphate Nutrition 0.000 claims description 2
- HYSLHVMRVBBRIG-UHFFFAOYSA-N 6-chloro-2-methyl-1h-pyrido[3,2-d]pyrimidin-4-one Chemical compound C1=C(Cl)N=C2C(=O)NC(C)=NC2=C1 HYSLHVMRVBBRIG-UHFFFAOYSA-N 0.000 claims 4
- 239000003937 drug carrier Substances 0.000 claims 2
- DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 claims 1
- 238000010533 azeotropic distillation Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 210000000988 bone and bone Anatomy 0.000 abstract description 2
- 239000000825 pharmaceutical preparation Substances 0.000 abstract description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 abstract description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 abstract 1
- 201000003068 rheumatic fever Diseases 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 34
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 17
- 239000002904 solvent Substances 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 238000010992 reflux Methods 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 208000006673 asthma Diseases 0.000 description 10
- 235000019441 ethanol Nutrition 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 210000002683 foot Anatomy 0.000 description 8
- 238000004128 high performance liquid chromatography Methods 0.000 description 8
- 230000002757 inflammatory effect Effects 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 7
- 208000004454 Hyperalgesia Diseases 0.000 description 7
- 208000035154 Hyperesthesia Diseases 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 210000004027 cell Anatomy 0.000 description 6
- 239000012065 filter cake Substances 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 208000023504 respiratory system disease Diseases 0.000 description 6
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 5
- 108050004388 Transient receptor potential cation channel subfamily V member 1 Proteins 0.000 description 5
- 102100029613 Transient receptor potential cation channel subfamily V member 1 Human genes 0.000 description 5
- 239000011575 calcium Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
- 239000012981 Hank's balanced salt solution Substances 0.000 description 4
- 101000633069 Homo sapiens Transient receptor potential cation channel subfamily V member 1 Proteins 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 206010061218 Inflammation Diseases 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 239000012131 assay buffer Substances 0.000 description 4
- 229910052791 calcium Inorganic materials 0.000 description 4
- YKPUWZUDDOIDPM-SOFGYWHQSA-N capsaicin Chemical compound COC1=CC(CNC(=O)CCCC\C=C\C(C)C)=CC=C1O YKPUWZUDDOIDPM-SOFGYWHQSA-N 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 102000045756 human TRPV1 Human genes 0.000 description 4
- 230000004054 inflammatory process Effects 0.000 description 4
- 230000014759 maintenance of location Effects 0.000 description 4
- 201000004624 Dermatitis Diseases 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 206010065390 Inflammatory pain Diseases 0.000 description 3
- 239000000556 agonist Substances 0.000 description 3
- 230000003110 anti-inflammatory effect Effects 0.000 description 3
- 238000003556 assay Methods 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 229910001873 dinitrogen Inorganic materials 0.000 description 3
- 238000010828 elution Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 230000000414 obstructive effect Effects 0.000 description 3
- 238000011552 rat model Methods 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 238000010561 standard procedure Methods 0.000 description 3
- IBHVWQOHJJPTNV-UHFFFAOYSA-N 1-(4-chlorophenyl)-3,3-dimethylbutan-2-imine;hydrochloride Chemical compound Cl.CC(C)(C)C(=N)CC1=CC=C(Cl)C=C1 IBHVWQOHJJPTNV-UHFFFAOYSA-N 0.000 description 2
- QATHVLKLWVUSRC-UHFFFAOYSA-N 4-methyl-1-phenylpentan-3-one Chemical compound CC(C)C(=O)CCC1=CC=CC=C1 QATHVLKLWVUSRC-UHFFFAOYSA-N 0.000 description 2
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 206010058019 Cancer Pain Diseases 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 206010009900 Colitis ulcerative Diseases 0.000 description 2
- 208000011231 Crohn disease Diseases 0.000 description 2
- 108010037462 Cyclooxygenase 2 Proteins 0.000 description 2
- 206010063057 Cystitis noninfective Diseases 0.000 description 2
- UGJMXCAKCUNAIE-UHFFFAOYSA-N Gabapentin Chemical compound OC(=O)CC1(CN)CCCCC1 UGJMXCAKCUNAIE-UHFFFAOYSA-N 0.000 description 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 description 2
- 102000004310 Ion Channels Human genes 0.000 description 2
- 108090000862 Ion Channels Proteins 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 208000019695 Migraine disease Diseases 0.000 description 2
- ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- PHVGLTMQBUFIQQ-UHFFFAOYSA-N Nortryptiline Chemical group C1CC2=CC=CC=C2C(=CCCNC)C2=CC=CC=C21 PHVGLTMQBUFIQQ-UHFFFAOYSA-N 0.000 description 2
- 206010033645 Pancreatitis Diseases 0.000 description 2
- 102100038280 Prostaglandin G/H synthase 2 Human genes 0.000 description 2
- 201000004681 Psoriasis Diseases 0.000 description 2
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 description 2
- 201000006704 Ulcerative Colitis Diseases 0.000 description 2
- 206010046851 Uveitis Diseases 0.000 description 2
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 description 2
- 201000000028 adult respiratory distress syndrome Diseases 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- KRMDCWKBEZIMAB-UHFFFAOYSA-N amitriptyline Chemical compound C1CC2=CC=CC=C2C(=CCCN(C)C)C2=CC=CC=C21 KRMDCWKBEZIMAB-UHFFFAOYSA-N 0.000 description 2
- 230000000202 analgesic effect Effects 0.000 description 2
- 239000000604 anti-edema agent Substances 0.000 description 2
- 230000003070 anti-hyperalgesia Effects 0.000 description 2
- 239000002260 anti-inflammatory agent Substances 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 208000010668 atopic eczema Diseases 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 230000003185 calcium uptake Effects 0.000 description 2
- 229960002504 capsaicin Drugs 0.000 description 2
- 235000017663 capsaicin Nutrition 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000003271 compound fluorescence assay Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 208000035475 disorder Diseases 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 150000002081 enamines Chemical class 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 150000003840 hydrochlorides Chemical class 0.000 description 2
- 208000013403 hyperactivity Diseases 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 208000027866 inflammatory disease Diseases 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- IUYHWZFSGMZEOG-UHFFFAOYSA-M magnesium;propane;chloride Chemical compound [Mg+2].[Cl-].C[CH-]C IUYHWZFSGMZEOG-UHFFFAOYSA-M 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 208000004296 neuralgia Diseases 0.000 description 2
- 208000021722 neuropathic pain Diseases 0.000 description 2
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 2
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- JAMNHZBIQDNHMM-UHFFFAOYSA-N pivalonitrile Chemical compound CC(C)(C)C#N JAMNHZBIQDNHMM-UHFFFAOYSA-N 0.000 description 2
- 206010035653 pneumoconiosis Diseases 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 230000002441 reversible effect Effects 0.000 description 2
- 208000017520 skin disease Diseases 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000001356 surgical procedure Methods 0.000 description 2
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- KQNBRMUBPRGXSL-UHFFFAOYSA-N 1-(bromomethyl)-4-chlorobenzene Chemical compound ClC1=CC=C(CBr)C=C1 KQNBRMUBPRGXSL-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- SXGZJKUKBWWHRA-UHFFFAOYSA-N 2-(N-morpholiniumyl)ethanesulfonate Chemical compound [O-]S(=O)(=O)CC[NH+]1CCOCC1 SXGZJKUKBWWHRA-UHFFFAOYSA-N 0.000 description 1
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 1
- MFEILWXBDBCWKF-UHFFFAOYSA-N 3-phenylpropanoyl chloride Chemical compound ClC(=O)CCC1=CC=CC=C1 MFEILWXBDBCWKF-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 1
- LNDZXOWGUAIUBG-UHFFFAOYSA-N 6-aminouracil Chemical compound NC1=CC(=O)NC(=O)N1 LNDZXOWGUAIUBG-UHFFFAOYSA-N 0.000 description 1
- QEQPTRDAKBTIGJ-UHFFFAOYSA-N 6-benzyl-7-propan-2-yl-1H-pyrido[2,3-d]pyrimidine-2,4-dione Chemical compound C(C1=CC=CC=C1)C1=CC2=C(NC(NC2=O)=O)N=C1C(C)C QEQPTRDAKBTIGJ-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- 208000006820 Arthralgia Diseases 0.000 description 1
- 208000033116 Asbestos intoxication Diseases 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- 206010006002 Bone pain Diseases 0.000 description 1
- 101800004538 Bradykinin Proteins 0.000 description 1
- 206010048962 Brain oedema Diseases 0.000 description 1
- 208000007596 Byssinosis Diseases 0.000 description 1
- 208000025480 CHILD syndrome Diseases 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- GDLIGKIOYRNHDA-UHFFFAOYSA-N Clomipramine Chemical compound C1CC2=CC=C(Cl)C=C2N(CCCN(C)C)C2=CC=CC=C21 GDLIGKIOYRNHDA-UHFFFAOYSA-N 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 206010011224 Cough Diseases 0.000 description 1
- 241000699802 Cricetulus griseus Species 0.000 description 1
- 229920000858 Cyclodextrin Polymers 0.000 description 1
- HCYAFALTSJYZDH-UHFFFAOYSA-N Desimpramine Chemical compound C1CC2=CC=CC=C2N(CCCNC)C2=CC=CC=C21 HCYAFALTSJYZDH-UHFFFAOYSA-N 0.000 description 1
- 208000005171 Dysmenorrhea Diseases 0.000 description 1
- 208000001640 Fibromyalgia Diseases 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- QXZGBUJJYSLZLT-UHFFFAOYSA-N H-Arg-Pro-Pro-Gly-Phe-Ser-Pro-Phe-Arg-OH Natural products NC(N)=NCCCC(N)C(=O)N1CCCC1C(=O)N1C(C(=O)NCC(=O)NC(CC=2C=CC=CC=2)C(=O)NC(CO)C(=O)N2C(CCC2)C(=O)NC(CC=2C=CC=CC=2)C(=O)NC(CCCN=C(N)N)C(O)=O)CCC1 QXZGBUJJYSLZLT-UHFFFAOYSA-N 0.000 description 1
- 239000007995 HEPES buffer Substances 0.000 description 1
- 208000027109 Headache disease Diseases 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- 208000005615 Interstitial Cystitis Diseases 0.000 description 1
- 208000028603 Interstitial lung disease specific to childhood Diseases 0.000 description 1
- 102100035792 Kininogen-1 Human genes 0.000 description 1
- 208000019693 Lung disease Diseases 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 208000007101 Muscle Cramp Diseases 0.000 description 1
- 208000029549 Muscle injury Diseases 0.000 description 1
- 208000000112 Myalgia Diseases 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 208000037656 Respiratory Sounds Diseases 0.000 description 1
- 206010039085 Rhinitis allergic Diseases 0.000 description 1
- 206010040070 Septic Shock Diseases 0.000 description 1
- 201000010001 Silicosis Diseases 0.000 description 1
- 208000005392 Spasm Diseases 0.000 description 1
- 208000010040 Sprains and Strains Diseases 0.000 description 1
- 229940123445 Tricyclic antidepressant Drugs 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 1
- 206010046543 Urinary incontinence Diseases 0.000 description 1
- 206010046823 Uterine spasm Diseases 0.000 description 1
- 206010047924 Wheezing Diseases 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 239000000464 adrenergic agent Substances 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 201000009961 allergic asthma Diseases 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 230000000172 allergic effect Effects 0.000 description 1
- 201000010105 allergic rhinitis Diseases 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 208000028462 aluminosis Diseases 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- QWGDMFLQWFTERH-UHFFFAOYSA-N amoxapine Chemical compound C12=CC(Cl)=CC=C2OC2=CC=CC=C2N=C1N1CCNCC1 QWGDMFLQWFTERH-UHFFFAOYSA-N 0.000 description 1
- 229940025141 anafranil Drugs 0.000 description 1
- 230000036592 analgesia Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 208000010123 anthracosis Diseases 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 229940125681 anticonvulsant agent Drugs 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 229940111131 antiinflammatory and antirheumatic product propionic acid derivative Drugs 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 206010003441 asbestosis Diseases 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229960000794 baclofen Drugs 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 239000012455 biphasic mixture Substances 0.000 description 1
- 239000002981 blocking agent Substances 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- QXZGBUJJYSLZLT-FDISYFBBSA-N bradykinin Chemical compound NC(=N)NCCC[C@H](N)C(=O)N1CCC[C@H]1C(=O)N1[C@H](C(=O)NCC(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CO)C(=O)N2[C@@H](CCC2)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)CCC1 QXZGBUJJYSLZLT-FDISYFBBSA-N 0.000 description 1
- 208000006752 brain edema Diseases 0.000 description 1
- 206010006451 bronchitis Diseases 0.000 description 1
- 230000003435 bronchoconstrictive effect Effects 0.000 description 1
- 229940124630 bronchodilator Drugs 0.000 description 1
- 239000000168 bronchodilator agent Substances 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- 229960000623 carbamazepine Drugs 0.000 description 1
- FFGPTBGBLSHEPO-UHFFFAOYSA-N carbamazepine Chemical compound C1=CC2=CC=CC=C2N(C(=O)N)C2=CC=CC=C21 FFGPTBGBLSHEPO-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 229960000590 celecoxib Drugs 0.000 description 1
- RZEKVGVHFLEQIL-UHFFFAOYSA-N celecoxib Chemical compound C1=CC(C)=CC=C1C1=CC(C(F)(F)F)=NN1C1=CC=C(S(N)(=O)=O)C=C1 RZEKVGVHFLEQIL-UHFFFAOYSA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 238000011278 co-treatment Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 239000003246 corticosteroid Substances 0.000 description 1
- 229960001334 corticosteroids Drugs 0.000 description 1
- 229940111134 coxibs Drugs 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 239000003255 cyclooxygenase 2 inhibitor Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000002027 dichloromethane extract Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 229940011681 elavil Drugs 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical compound CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 230000000763 evoking effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- YFHXZQPUBCBNIP-UHFFFAOYSA-N fura-2 Chemical compound CC1=CC=C(N(CC(O)=O)CC(O)=O)C(OCCOC=2C(=CC=3OC(=CC=3C=2)C=2OC(=CN=2)C(O)=O)N(CC(O)=O)CC(O)=O)=C1 YFHXZQPUBCBNIP-UHFFFAOYSA-N 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 229960002870 gabapentin Drugs 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 238000002682 general surgery Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 231100000869 headache Toxicity 0.000 description 1
- KWHDXJHBFYQOTK-UHFFFAOYSA-N heptane;toluene Chemical compound CCCCCCC.CC1=CC=CC=C1 KWHDXJHBFYQOTK-UHFFFAOYSA-N 0.000 description 1
- 210000000548 hind-foot Anatomy 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000036543 hypotension Effects 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- BCGWQEUPMDMJNV-UHFFFAOYSA-N imipramine Chemical compound C1CC2=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C21 BCGWQEUPMDMJNV-UHFFFAOYSA-N 0.000 description 1
- XZZXIYZZBJDEEP-UHFFFAOYSA-N imipramine hydrochloride Chemical compound [Cl-].C1CC2=CC=CC=C2N(CCC[NH+](C)C)C2=CC=CC=C21 XZZXIYZZBJDEEP-UHFFFAOYSA-N 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 201000006334 interstitial nephritis Diseases 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 201000010659 intrinsic asthma Diseases 0.000 description 1
- 208000002551 irritable bowel syndrome Diseases 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 239000004530 micro-emulsion Substances 0.000 description 1
- 206010027599 migraine Diseases 0.000 description 1
- 239000003068 molecular probe Substances 0.000 description 1
- 208000013465 muscle pain Diseases 0.000 description 1
- HXRAMSFGUAOAJR-UHFFFAOYSA-N n,n,n',n'-tetramethyl-1-[(2-methylpropan-2-yl)oxy]methanediamine Chemical compound CN(C)C(N(C)C)OC(C)(C)C HXRAMSFGUAOAJR-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229940087480 norpramin Drugs 0.000 description 1
- 208000007892 occupational asthma Diseases 0.000 description 1
- 208000014055 occupational lung disease Diseases 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 210000001672 ovary Anatomy 0.000 description 1
- CTRLABGOLIVAIY-UHFFFAOYSA-N oxcarbazepine Chemical compound C1C(=O)C2=CC=CC=C2N(C(=O)N)C2=CC=CC=C21 CTRLABGOLIVAIY-UHFFFAOYSA-N 0.000 description 1
- 229960001816 oxcarbazepine Drugs 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 230000008058 pain sensation Effects 0.000 description 1
- 229940055692 pamelor Drugs 0.000 description 1
- 208000033808 peripheral neuropathy Diseases 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 210000002381 plasma Anatomy 0.000 description 1
- 239000008389 polyethoxylated castor oil Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 230000002980 postoperative effect Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 1
- OGQDIIKRQRZXJH-UHFFFAOYSA-N protriptyline hydrochloride Chemical compound [Cl-].C1=CC2=CC=CC=C2C(CCC[NH2+]C)C2=CC=CC=C21 OGQDIIKRQRZXJH-UHFFFAOYSA-N 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 206010039083 rhinitis Diseases 0.000 description 1
- 229960000371 rofecoxib Drugs 0.000 description 1
- RZJQGNCSTQAWON-UHFFFAOYSA-N rofecoxib Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC=CC=2)C(=O)OC1 RZJQGNCSTQAWON-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
- 210000003497 sciatic nerve Anatomy 0.000 description 1
- 230000036303 septic shock Effects 0.000 description 1
- 208000004003 siderosis Diseases 0.000 description 1
- 239000000050 smooth muscle relaxant Substances 0.000 description 1
- WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- PODWXQQNRWNDGD-UHFFFAOYSA-L sodium thiosulfate pentahydrate Chemical compound O.O.O.O.O.[Na+].[Na+].[O-]S([S-])(=O)=O PODWXQQNRWNDGD-UHFFFAOYSA-L 0.000 description 1
- 239000007962 solid dispersion Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000007655 standard test method Methods 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 238000011477 surgical intervention Methods 0.000 description 1
- 239000012730 sustained-release form Substances 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229940041597 tofranil Drugs 0.000 description 1
- 229940035276 tofranil-pm Drugs 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
- 239000003029 tricyclic antidepressant agent Substances 0.000 description 1
- 208000001319 vasomotor rhinitis Diseases 0.000 description 1
- 208000037911 visceral disease Diseases 0.000 description 1
- 229940045977 vivactil Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/18—Drugs for disorders of the alimentary tract or the digestive system for pancreatic disorders, e.g. pancreatic enzymes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/02—Nasal agents, e.g. decongestants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/14—Antitussive agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/10—Drugs for disorders of the urinary system of the bladder
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/04—Antipruritics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/06—Antigout agents, e.g. antihyperuricemic or uricosuric agents
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
-
- 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]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Pulmonology (AREA)
- Pain & Pain Management (AREA)
- Neurosurgery (AREA)
- Dermatology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Rheumatology (AREA)
- Urology & Nephrology (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Immunology (AREA)
- Physical Education & Sports Medicine (AREA)
- Vascular Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Otolaryngology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0107505A GB0107505D0 (en) | 2001-03-26 | 2001-03-26 | Organic compounds |
| US33828101P | 2001-12-06 | 2001-12-06 | |
| PCT/EP2002/003332 WO2002076946A2 (en) | 2001-03-26 | 2002-03-25 | Fused pyridine derivatives for use as vanilloid receptor antagonists for treating pain. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HUP0303623A2 true HUP0303623A2 (hu) | 2004-03-01 |
Family
ID=26245894
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU0303623A HUP0303623A2 (hu) | 2001-03-26 | 2002-03-25 | Kondenzált piridinszármazékok, eljárás az előállításukra és ezeket tartalmazó gyógyászati készítmények vanilloid receptor antagonistaként fájdalom kezelésére |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US7915264B2 (https=) |
| EP (1) | EP1377576A2 (https=) |
| JP (1) | JP4205430B2 (https=) |
| KR (1) | KR20030083755A (https=) |
| CN (1) | CN1500089A (https=) |
| BR (1) | BR0208338A (https=) |
| CA (1) | CA2441599A1 (https=) |
| CZ (1) | CZ20032561A3 (https=) |
| HU (1) | HUP0303623A2 (https=) |
| IL (1) | IL157815A0 (https=) |
| MX (1) | MXPA03008754A (https=) |
| NO (1) | NO326546B1 (https=) |
| PE (1) | PE20021161A1 (https=) |
| PL (1) | PL363907A1 (https=) |
| RU (1) | RU2003130221A (https=) |
| SK (1) | SK11952003A3 (https=) |
| WO (1) | WO2002076946A2 (https=) |
Families Citing this family (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE328868T1 (de) | 2000-08-21 | 2006-06-15 | Pacific Corp | Neue (thio)harnstoffverbindungen und arzneimittelkompositionen, die diese enthalten |
| CA2417507A1 (en) | 2000-08-21 | 2002-02-28 | Pacific Corporation | Novel thiourea derivatives and the pharmaceutical compositions containing the same |
| HUP0500200A2 (hu) | 2002-01-17 | 2005-07-28 | Neurogen Corporation | Szubsztituált kinazolin-4-ilamin analógok, mint kapszaicin modulátorok és ezeket tartalmazó gyógyszerkészítmények |
| US7071335B2 (en) | 2002-02-01 | 2006-07-04 | Euro-Celtique S.A. | 2-pyridinyl-1-piperazine therapeutic agents useful for treating pain |
| US6864261B2 (en) | 2002-05-02 | 2005-03-08 | Euro-Celtique S.A. | Therapeutic agents useful for treating pain |
| GB0229808D0 (en) * | 2002-12-20 | 2003-01-29 | Glaxo Group Ltd | Novel compositions |
| EP1606289B1 (en) | 2003-02-14 | 2009-12-02 | Glaxo Group Limited | Carboxamide derivatives |
| EP1627869B1 (en) | 2003-05-20 | 2012-05-02 | Ajinomoto Co., Inc. | Vanilloid receptor modulators |
| GB0319150D0 (en) | 2003-08-14 | 2003-09-17 | Glaxo Group Ltd | Novel compounds |
| CA2545725A1 (en) | 2003-11-14 | 2005-06-02 | Merck Sharp & Dohme Limited | Bicyclic pyrimidin-4-(3h)-ones and analogues and derivatives thereof which modulate the function of the vanilloid-1 receptor (vr1) |
| GB0412769D0 (en) | 2004-06-08 | 2004-07-07 | Novartis Ag | Organic compounds |
| WO2006019965A2 (en) * | 2004-07-16 | 2006-02-23 | Takeda San Diego, Inc. | Dipeptidyl peptidase inhibitors |
| US7879866B2 (en) | 2004-07-19 | 2011-02-01 | Dorte Xenia Gram | Inhibition of the activity of the capsaicin receptor in the treatment of obesity or obesity-related diseases and disorders |
| DE102004039373A1 (de) | 2004-08-12 | 2006-02-23 | Grünenthal GmbH | Para-Alkyl-substituierte N-(4-Hydroxy-3-methoxy-benzyl)-zimtsäureamide und deren Verwendung zur Herstellung von Arzneimitteln |
| KR20060087386A (ko) | 2005-01-28 | 2006-08-02 | 주식회사 대웅제약 | 신규 벤조이미다졸 유도체 및 이를 함유하는 약제학적조성물 |
| WO2006098554A1 (en) * | 2005-03-16 | 2006-09-21 | Amorepacific Corporation | Novel compounds, isomer thereof or pharmaceutically acceptable salts thereof as vanilloid receptor antagonist; and a pharmaceutical composition containing the same |
| GB0506147D0 (en) * | 2005-03-24 | 2005-05-04 | Merck Sharp & Dohme | Therapeutic agents |
| US20090298856A1 (en) * | 2005-05-11 | 2009-12-03 | Rebecca Elizabeth Brown | 2,3 Substituted fused bicyclic pyrimidin-4(3H)-ones modulating the function of the vanilliod-1receptor (VR1) |
| GB0509573D0 (en) * | 2005-05-11 | 2005-06-15 | Merck Sharp & Dohme | Therapeutic compounds |
| DK1940821T3 (da) * | 2005-10-19 | 2013-06-10 | Gruenenthal Gmbh | Nye vanilloid-receptorligander og deres anvendelse til fremstilling af lægemidler. |
| GB0525068D0 (en) | 2005-12-08 | 2006-01-18 | Novartis Ag | Organic compounds |
| KR100761222B1 (ko) * | 2006-03-08 | 2007-10-04 | 성균관대학교산학협력단 | 약물의존중독을 예방 및 치료하기 위한 바닐로이드 수용체길항제 |
| GB0614471D0 (en) | 2006-07-20 | 2006-08-30 | Syngenta Ltd | Herbicidal Compounds |
| CA2660957C (en) | 2006-08-23 | 2016-10-11 | Neurogen Corporation | 2-phenoxy pyrimidinone analogues |
| US20080207659A1 (en) | 2007-02-15 | 2008-08-28 | Asit Kumar Chakraborti | Inhibitors of phosphodiesterase type 4 |
| CL2008001112A1 (es) * | 2007-04-20 | 2008-12-19 | Novartis Ag | Usos de compuestos derivados de pirido[2,3-d]pirimidin-4-ona para tratar comezon o un trastorno relacionado con comezon; combinacion de los compuestos con otro farmaco; y uso de la combinacion para tratar la comezon o un trastorno relacionado con comezon. |
| KR20100039410A (ko) * | 2007-07-18 | 2010-04-15 | 노파르티스 아게 | Ｖｒ－１ 길항제 및 ｃｏｘ－２ 억제제의 상승적 조합물 |
| CA2724008A1 (en) * | 2008-01-11 | 2009-09-11 | Glenmark Pharmaceuticals, S.A. | Fused pyrimidine derivatives as trpv3 modulators |
| WO2009121036A2 (en) * | 2008-03-27 | 2009-10-01 | Neurogen Corporation | Substituted aryl pyrimidinone derivatives |
| JP5372138B2 (ja) | 2008-04-18 | 2013-12-18 | テウン ファーマシューティカル カンパニー，リミテッド | 新規ベンゾオキサジンベンズイミダゾール誘導体、これを含む薬学組成物およびこの用途 |
| US8349852B2 (en) | 2009-01-13 | 2013-01-08 | Novartis Ag | Quinazolinone derivatives useful as vanilloid antagonists |
| AR080056A1 (es) | 2010-02-01 | 2012-03-07 | Novartis Ag | Derivados de ciclohexil-amida como antagonistas de los receptores de crf |
| JP2013518085A (ja) | 2010-02-01 | 2013-05-20 | ノバルティス アーゲー | ＣＲＦ−１受容体アンタゴニストとしてのピラゾロ［５，１ｂ］オキサゾール誘導体 |
| JP5748777B2 (ja) | 2010-02-02 | 2015-07-15 | ノバルティス アーゲー | Ｃｒｆ受容体アンタゴニストとしてのシクロヘキシルアミド誘導体 |
| KR101293384B1 (ko) | 2010-10-13 | 2013-08-05 | 주식회사 대웅제약 | 신규 피리딜 벤조옥사진 유도체, 이를 포함하는 약학 조성물 및 이의 용도 |
| UY34094A (es) | 2011-05-27 | 2013-01-03 | Novartis Ag | Derivados de la piperidina 3-espirocíclica como agonistas de receptores de la ghrelina |
| CA2867043A1 (en) | 2012-05-03 | 2013-11-07 | Novartis Ag | L-malate salt of 2,7-diaza-spiro[4.5]dec-7-yle derivatives and crystalline forms thereof as ghrelin receptor agonists |
| EP3204347B1 (en) | 2015-12-23 | 2024-10-23 | Commonwealth Scientific and Industrial Research Organisation | Enamine compounds for protecting against uv radiation |
| CN111393380A (zh) * | 2018-07-09 | 2020-07-10 | 湖南博隽生物医药有限公司 | 一种用于治疗慢性炎性痛的辣椒素受体拮抗剂 |
| DE102022104759A1 (de) | 2022-02-28 | 2023-08-31 | SCi Kontor GmbH | Co-Kristall-Screening Verfahren, insbesondere zur Herstellung von Co-Kristallen |
| CN114605408B (zh) * | 2022-03-30 | 2023-06-16 | 沈阳药科大学 | 5-羟基-1,3-二取代苯基吡啶并[2,3-d]嘧啶类化合物及其制法和应用 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2749344A (en) | 1953-01-02 | 1956-06-05 | Burroughs Wellcome Co | Pyrimidine compounds |
| US5958930A (en) | 1991-04-08 | 1999-09-28 | Duquesne University Of The Holy Ghost | Pyrrolo pyrimidine and furo pyrimidine derivatives |
| EP0743855A1 (en) | 1994-01-03 | 1996-11-27 | Acea Pharmaceuticals, Inc. | 8-aza, 6-aza and 6,8-diaza-1,4-dihydroquinoxaline-2,3-diones and the use thereof as antagonists for the glycine/nmda receptor |
| FR2750862B1 (fr) | 1996-07-12 | 1998-10-16 | Dupin Jean Pierre | Utilisation d'heterocycles diazotes fusionnes avec un systeme aromatique ou heteroaromatique pour le traitement des maladies thrombo-emboliques |
-
2002
- 2002-03-25 PL PL02363907A patent/PL363907A1/xx not_active Application Discontinuation
- 2002-03-25 BR BR0208338-8A patent/BR0208338A/pt not_active IP Right Cessation
- 2002-03-25 CN CNA028073495A patent/CN1500089A/zh active Pending
- 2002-03-25 SK SK1195-2003A patent/SK11952003A3/sk unknown
- 2002-03-25 JP JP2002576207A patent/JP4205430B2/ja not_active Expired - Fee Related
- 2002-03-25 EP EP02730062A patent/EP1377576A2/en not_active Withdrawn
- 2002-03-25 WO PCT/EP2002/003332 patent/WO2002076946A2/en not_active Ceased
- 2002-03-25 CZ CZ20032561A patent/CZ20032561A3/cs unknown
- 2002-03-25 MX MXPA03008754A patent/MXPA03008754A/es not_active Application Discontinuation
- 2002-03-25 IL IL15781502A patent/IL157815A0/xx unknown
- 2002-03-25 RU RU2003130221/04A patent/RU2003130221A/ru not_active Application Discontinuation
- 2002-03-25 US US10/469,756 patent/US7915264B2/en not_active Expired - Fee Related
- 2002-03-25 KR KR10-2003-7012460A patent/KR20030083755A/ko not_active Ceased
- 2002-03-25 HU HU0303623A patent/HUP0303623A2/hu unknown
- 2002-03-25 CA CA002441599A patent/CA2441599A1/en not_active Abandoned
- 2002-03-26 PE PE2002000241A patent/PE20021161A1/es not_active Application Discontinuation
-
2003
- 2003-09-16 NO NO20034122A patent/NO326546B1/no not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CA2441599A1 (en) | 2002-10-03 |
| PE20021161A1 (es) | 2003-02-21 |
| IL157815A0 (en) | 2004-03-28 |
| JP2004528312A (ja) | 2004-09-16 |
| US7915264B2 (en) | 2011-03-29 |
| US20040138454A1 (en) | 2004-07-15 |
| JP4205430B2 (ja) | 2009-01-07 |
| PL363907A1 (en) | 2004-11-29 |
| KR20030083755A (ko) | 2003-10-30 |
| NO20034122L (no) | 2003-09-16 |
| BR0208338A (pt) | 2004-03-09 |
| SK11952003A3 (sk) | 2004-03-02 |
| NO20034122D0 (no) | 2003-09-16 |
| RU2003130221A (ru) | 2005-04-10 |
| WO2002076946A2 (en) | 2002-10-03 |
| EP1377576A2 (en) | 2004-01-07 |
| CN1500089A (zh) | 2004-05-26 |
| NO326546B1 (no) | 2009-01-05 |
| CZ20032561A3 (cs) | 2003-12-17 |
| MXPA03008754A (es) | 2004-02-18 |
| WO2002076946A3 (en) | 2002-12-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| HUP0303623A2 (hu) | Kondenzált piridinszármazékok, eljárás az előállításukra és ezeket tartalmazó gyógyászati készítmények vanilloid receptor antagonistaként fájdalom kezelésére | |
| Campbell et al. | 2, 4-Diamino-6, 7-dimethoxyquinoline derivatives as. alpha. 1-adrenoceptor antagonists and antihypertensive agents | |
| ES2761572T3 (es) | Derivados de pirimidina como inhibidores de quinasa | |
| JP5602728B2 (ja) | キナゾリノン誘導体の製造方法 | |
| ZA200302916B (en) | Naphthalene derivatives. | |
| RU2010129910A (ru) | 8-анилиноимидазопиридины и способы их использования | |
| AU754607B2 (en) | Phenanthroline derivatives | |
| CA2814120C (en) | Novel anti-cancer agents | |
| ES2354039T3 (es) | Derivados de n-aril-{4-[7-(alcoxi)quinazolin-4-il]piperazinil}carboxamida como inhibidores de pdgfr. | |
| AU2011271480B2 (en) | Riminophenazines with 2-(heteroaryl)amino substituents and their anti-microbial activity | |
| CN115996911A (zh) | 具有p2x4受体拮抗活性的取代的n-苯乙酰胺 | |
| JP3426242B2 (ja) | ジアザシクロアルカンアルキルスルホンアミド誘導体 | |
| WO2015148465A1 (en) | Pyrazole compounds selective for neurotensin 2 receptor | |
| BG107219A (bg) | Терапевтично приложими нови соли на сск инхибитори, методи за тяхното получаване и фармацевтични състави, които ги съдържат | |
| CN110229150B (zh) | 咪唑并[4,5-c]吡啶类衍生物及其用途 | |
| JP2010513455A (ja) | Ｔｒｐｖ１受容体拮抗薬としてのｏ−置換ジベンジル尿素誘導体 | |
| US6706705B1 (en) | Quinazoline derivatives | |
| AU2002302469A1 (en) | Fused pyridine derivatives for use as vanilloid receptor antagonists for treating pain. | |
| US20040259881A1 (en) | Nitrogenous heterocyclic compounds | |
| US6602897B2 (en) | m-Amino-phenylimino-imidazolidine derivatives for treating urinary incontinence | |
| US20010046991A1 (en) | Derivatives of quinoline as alpha-2 antagonists | |
| AU2011235290B2 (en) | Purine compounds used as CB2 agonists | |
| EP4506346A1 (en) | Thiobenzimidazole derivative or pharmaceutically acceptable salt thereof, and use thereof | |
| ZA200306636B (en) | Fused pyridine derivatives for use as vanilloid receptor antagonists for treating pain. | |
| CS214797B2 (cs) | Způsob výroby nových derivátů 4-amino-2-piperidinochinazolinu |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FD9A | Lapse of provisional protection due to non-payment of fees |