ZA200508948B - Substituted pyrazoles - Google Patents
Substituted pyrazoles Download PDFInfo
- Publication number
- ZA200508948B ZA200508948B ZA200508948A ZA200508948A ZA200508948B ZA 200508948 B ZA200508948 B ZA 200508948B ZA 200508948 A ZA200508948 A ZA 200508948A ZA 200508948 A ZA200508948 A ZA 200508948A ZA 200508948 B ZA200508948 B ZA 200508948B
- Authority
- ZA
- South Africa
- Prior art keywords
- pyrazol
- fluorophenyl
- biphenyl
- methyl
- het
- Prior art date
Links
- 150000003217 pyrazoles Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 78
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 69
- -1 ethyl- Chemical group 0.000 claims description 45
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 42
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 26
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 23
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 238000011282 treatment Methods 0.000 claims description 19
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 18
- 239000003814 drug Substances 0.000 claims description 18
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 16
- 101150065749 Churc1 gene Proteins 0.000 claims description 16
- 102100038239 Protein Churchill Human genes 0.000 claims description 16
- 239000012453 solvate Substances 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 238000011321 prophylaxis Methods 0.000 claims description 9
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 7
- 201000010099 disease Diseases 0.000 claims description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 6
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
- 102000040125 5-hydroxytryptamine receptor family Human genes 0.000 claims description 5
- 108091032151 5-hydroxytryptamine receptor family Proteins 0.000 claims description 5
- 230000009471 action Effects 0.000 claims description 5
- GFDFZTFQPIBNSQ-WSBLSWJJSA-N jamine Chemical compound C([C@H]([C@H]12)C3)CCN2CN2CCCC[C@@H]2[C@]21CN1CCCC[C@@H]1[C@H]3C2 GFDFZTFQPIBNSQ-WSBLSWJJSA-N 0.000 claims description 5
- GFDFZTFQPIBNSQ-UHFFFAOYSA-N (+)-homo-18-epiormosanine Natural products C1C(C23)CCCN3CN3CCCCC3C32CN2CCCCC2C1C3 GFDFZTFQPIBNSQ-UHFFFAOYSA-N 0.000 claims description 4
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=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
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 4
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 4
- RJWLLQWLBMJCFD-UHFFFAOYSA-N 4-methylpiperazin-1-amine Chemical compound CN1CCN(N)CC1 RJWLLQWLBMJCFD-UHFFFAOYSA-N 0.000 claims description 4
- GFDFZTFQPIBNSQ-LDIYZUBKSA-N Homoormosanine Natural products N12[C@H]3[C@H](C[C@H]4[C@@H]5N(C[C@@]3([C@@H]3N(C1)CCCC3)C4)CCCC5)CCC2 GFDFZTFQPIBNSQ-LDIYZUBKSA-N 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 4
- AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 claims description 4
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 4
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
- KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical compound [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 claims description 3
- CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 claims 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 claims description 3
- 208000000103 Anorexia Nervosa Diseases 0.000 claims description 3
- 208000032841 Bulimia Diseases 0.000 claims description 3
- 206010006550 Bulimia nervosa Diseases 0.000 claims description 3
- 208000030814 Eating disease Diseases 0.000 claims description 3
- 208000019454 Feeding and Eating disease Diseases 0.000 claims description 3
- 208000028017 Psychotic disease Diseases 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 3
- 229960003529 diazepam Drugs 0.000 claims description 3
- 235000014632 disordered eating Nutrition 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 3
- 125000004944 pyrazin-3-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 claims description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000004361 3,4,5-trifluorophenyl group Chemical group [H]C1=C(F)C(F)=C(F)C([H])=C1* 0.000 claims description 2
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- 208000012902 Nervous system disease Diseases 0.000 claims description 2
- 208000025966 Neurological disease Diseases 0.000 claims description 2
- 206010036618 Premenstrual syndrome Diseases 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- 229920000728 polyester Polymers 0.000 claims 1
- 235000013350 formula milk Nutrition 0.000 description 48
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 40
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 31
- 239000000203 mixture Substances 0.000 description 27
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 23
- 229940022663 acetate Drugs 0.000 description 22
- 239000000243 solution Substances 0.000 description 21
- 238000010626 work up procedure Methods 0.000 description 20
- 235000011054 acetic acid Nutrition 0.000 description 16
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
- 229940113083 morpholine Drugs 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 150000003254 radicals Chemical class 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 11
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 7
- 239000004480 active ingredient Substances 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 102000049773 5-HT2A Serotonin Receptor Human genes 0.000 description 6
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Chemical compound OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- RFIOZSIHFNEKFF-UHFFFAOYSA-M piperazine-1-carboxylate Chemical compound [O-]C(=O)N1CCNCC1 RFIOZSIHFNEKFF-UHFFFAOYSA-M 0.000 description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 5
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 5
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- CUYKNJBYIJFRCU-UHFFFAOYSA-N pyridine-3-amine Natural products NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 101150104779 HTR2A gene Proteins 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000012442 inert solvent Substances 0.000 description 4
- SRJOCJYGOFTFLH-UHFFFAOYSA-N isonipecotic acid Chemical compound OC(=O)C1CCNCC1 SRJOCJYGOFTFLH-UHFFFAOYSA-N 0.000 description 4
- 239000012280 lithium aluminium hydride Substances 0.000 description 4
- 239000011572 manganese Substances 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- VLJNHYLEOZPXFW-UHFFFAOYSA-N pyrrolidine-2-carboxamide Chemical compound NC(=O)C1CCCN1 VLJNHYLEOZPXFW-UHFFFAOYSA-N 0.000 description 4
- 102000005962 receptors Human genes 0.000 description 4
- 108020003175 receptors Proteins 0.000 description 4
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 4
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 3
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- JQTMGOLZSBTZMS-UHFFFAOYSA-N 4-methylpiperazine-1-carbaldehyde Chemical compound CN1CCN(C=O)CC1 JQTMGOLZSBTZMS-UHFFFAOYSA-N 0.000 description 2
- VRJHQPZVIGNGMX-UHFFFAOYSA-N 4-piperidinone Chemical compound O=C1CCNCC1 VRJHQPZVIGNGMX-UHFFFAOYSA-N 0.000 description 2
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- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
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- 241001135382 Hypostomus agna Species 0.000 description 2
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- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
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- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
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- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
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- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
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- C—CHEMISTRY; METALLURGY
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- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
- C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
- C07D451/06—Oxygen atoms
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- 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
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- 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
- C07D471/10—Spiro-condensed systems
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- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/08—Bridged systems
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- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/08—Bridged systems
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Applications Claiming Priority (1)
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| DE10315572A DE10315572A1 (de) | 2003-04-05 | 2003-04-05 | Substituierte Pyrazole |
Publications (1)
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| DE10315571A1 (de) * | 2003-04-05 | 2004-10-14 | Merck Patent Gmbh | Pyrazolverbindungen |
| DE10315569A1 (de) * | 2003-04-05 | 2004-10-14 | Merck Patent Gmbh | Substituierte Pyrazolverbindungen |
| DE10315573A1 (de) | 2003-04-05 | 2004-10-14 | Merck Patent Gmbh | Substituierte Pyrazole |
| EP1669348A4 (en) | 2003-09-30 | 2009-03-11 | Eisai R&D Man Co Ltd | NEW ANTIPILIC AGENT CONTAINING A HETEROCYCLIC COMPOUND |
| EP1670460B1 (en) * | 2003-10-10 | 2014-11-26 | Bristol-Myers Squibb Company | Pyrazole derivatives as cannabinoid receptor modulators |
| US20050241110A1 (en) * | 2004-04-09 | 2005-11-03 | Bruce Baker | Ergonomic handles, especially for garden tools |
| US20090227799A1 (en) * | 2004-08-09 | 2009-09-10 | Kazutaka Nakamoto | Novel Antimalarial Agent Containing Heterocyclic Compound |
| JP4874958B2 (ja) | 2005-03-30 | 2012-02-15 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | ピリジン誘導体を含有する抗真菌剤 |
| TWI385169B (zh) | 2005-10-31 | 2013-02-11 | Eisai R&D Man Co Ltd | 經雜環取代之吡啶衍生物及含有彼之抗真菌劑 |
| AU2006309762B2 (en) | 2005-10-31 | 2010-02-25 | Eisai R&D Management Co., Ltd. | Heterocyclic substituted pyridine derivatives and antifungal agent containing same |
| GB0524814D0 (en) * | 2005-12-05 | 2006-01-11 | Glaxo Group Ltd | Compounds |
| WO2007120600A2 (en) * | 2006-04-10 | 2007-10-25 | Arena Pharmaceuticals, Inc. | 3-pyridinyl-pyrazole derivatives as modulators of the 5-ht2a serotonin receptor useful for the treatment of disorders related thereto |
| EP2065377B1 (en) | 2006-09-21 | 2011-11-23 | Eisai R&D Management Co., Ltd. | Pyridine derivative substituted by heteroaryl ring, and antifungal agent comprising the same |
| EP1938686A1 (de) * | 2006-12-29 | 2008-07-02 | Bayer CropScience AG | Substituierte 1-(3-Pyridinyl)pyrazol-4-yl-essigsäuren, Verfahren zu deren Herstellung und deren Verwendung als Herbizide und Pflanzenwachstumsregulatoren |
| TW200841879A (en) | 2007-04-27 | 2008-11-01 | Eisai R&D Man Co Ltd | Pyridine derivatives substituted by heterocyclic ring and phosphonoamino group, and anti-fungal agent containing same |
| CN102702185A (zh) | 2007-04-27 | 2012-10-03 | 卫材R&D管理有限公司 | 杂环取代吡啶衍生物的盐的结晶 |
| US7977358B2 (en) | 2007-07-26 | 2011-07-12 | Hoffmann-La Roche Inc. | Pyrazol derivatives |
| US8513287B2 (en) | 2007-12-27 | 2013-08-20 | Eisai R&D Management Co., Ltd. | Heterocyclic ring and phosphonoxymethyl group substituted pyridine derivatives and antifungal agent containing same |
| EP2135865A1 (de) | 2008-06-17 | 2009-12-23 | Bayer CropScience AG | Substituierte 1-(Diazinyl) pyrazol-4-yl-essigsäuren, Verfahren zu deren Herstellung und deren Verwendung als Herbizide und Pflanzenwachstumsregulatoren |
| WO2010032874A1 (ja) * | 2008-09-19 | 2010-03-25 | 住友化学株式会社 | 農業用組成物 |
| US8188119B2 (en) * | 2008-10-24 | 2012-05-29 | Eisai R&D Management Co., Ltd | Pyridine derivatives substituted with heterocyclic ring and γ-glutamylamino group, and antifungal agents containing same |
| EP2194052A1 (de) | 2008-12-06 | 2010-06-09 | Bayer CropScience AG | Substituierte 1-(Thiazolyl)- und 1-(Isothiazolyl)pyrazol-4-yl-essigsäuren, Verfahren zu deren Herstellung und deren Verwendung als Herbizide und Pflanzenwachstumsregulatoren |
| WO2011073098A1 (de) | 2009-12-15 | 2011-06-23 | Bayer Cropscience Ag | 1-(heteroaryl)-pyrazol-4-yl-essigsäuren, verfahren zu deren herstellung und deren verwendung als herbizide und pflanzenwachstumsregulatoren |
| JP5722891B2 (ja) | 2010-07-15 | 2015-05-27 | 大日本住友製薬株式会社 | ピラゾール化合物 |
| US9120757B2 (en) | 2013-03-14 | 2015-09-01 | Epizyme, Inc. | Arginine methyltransferase inhibitors and uses thereof |
| EP2970136A1 (en) | 2013-03-14 | 2016-01-20 | Epizyme, Inc. | Arginine methyl transferase inhibtors and uses thereof |
| US20160031839A1 (en) | 2013-03-14 | 2016-02-04 | Epizyme, Inc. | Arginine methyltransferase inhibitors and uses thereof |
| WO2014144659A1 (en) | 2013-03-14 | 2014-09-18 | Epizyme, Inc. | Pyrazole derivatives as prmt1 inhibitors and uses thereof |
| WO2014153208A1 (en) | 2013-03-14 | 2014-09-25 | Epizyme, Inc. | Arginine methyltransferase inhibitors and uses thereof |
| US9394258B2 (en) | 2013-03-14 | 2016-07-19 | Epizyme, Inc. | Arginine methyltransferase inhibitors and uses thereof |
| EP2970133B1 (en) | 2013-03-14 | 2018-10-24 | Epizyme, Inc. | Pyrazole derivatives as prmt1 inhibitors and uses thereof |
| SG11201506972PA (en) | 2013-03-14 | 2015-10-29 | Epizyme Inc | Arginine methyltransferase inhibitors and uses thereof |
| EP2970134B1 (en) | 2013-03-14 | 2018-02-28 | Epizyme, Inc. | Pyrazole derivatives as prmt1 inhibitors and uses thereof |
| AU2014260433A1 (en) | 2013-03-14 | 2015-09-10 | Epizyme, Inc. | Pyrazole derivatives as arginine methyltransferase inhibitors and uses thereof |
| EP3886854A4 (en) | 2018-11-30 | 2022-07-06 | Nuvation Bio Inc. | Pyrrole and pyrazole compounds and methods of use thereof |
| CN116554144A (zh) * | 2022-01-27 | 2023-08-08 | 司马健 | 一种sj系列芳基苯胺类化合物及其制备方法与医药用途 |
| DE202022104072U1 (de) | 2022-07-19 | 2022-07-29 | Siva Subramanian Narayanasamy | Heterozyklisch substituierte pyridinderivate antimykotische Mittel |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4146721A (en) * | 1969-09-12 | 1979-03-27 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Pyrazol-4-acetic acid compounds |
| BE793955A (fr) * | 1972-01-15 | 1973-07-12 | Merck Patent Gmbh | Arylpiperazines et leur procede de preparation |
| DE2906252A1 (de) * | 1979-02-19 | 1980-08-28 | Merck Patent Gmbh | Pyrazolderivate, diese enthaltende pharmazeutische zubereitungen und verfahren zu ihrer herstellung |
| US4631343A (en) * | 1983-11-07 | 1986-12-23 | Eli Lilly And Company | Cyanopyrazole intermediates |
| US6011028A (en) * | 1995-04-20 | 2000-01-04 | G.D. Searle & Co. | Cyclic amidino agents useful as nitric oxide synthase inhibitors |
| US6150393A (en) * | 1998-12-18 | 2000-11-21 | Arena Pharmaceuticals, Inc. | Small molecule modulators of non-endogenous, constitutively activated human serotonin receptors |
| US20010044445A1 (en) * | 1999-04-08 | 2001-11-22 | Bamaung Nwe Y. | Azole inhibitors of cytokine production |
| US6632815B2 (en) * | 1999-09-17 | 2003-10-14 | Millennium Pharmaceuticals, Inc. | Inhibitors of factor Xa |
| US7067507B2 (en) * | 2001-06-12 | 2006-06-27 | Pharmacia & Upjohn Company | Macrocycles useful in the treatment of Alzheimer's disease |
| DE10149370A1 (de) * | 2001-10-06 | 2003-04-10 | Merck Patent Gmbh | Pyrazolderivate |
| EP1494664A2 (en) * | 2002-04-18 | 2005-01-12 | Pharmacia Corporation | Combinations of cox-2 inhibitors and other agents for the treatment of parkinson's disease |
| DE10315573A1 (de) * | 2003-04-05 | 2004-10-14 | Merck Patent Gmbh | Substituierte Pyrazole |
| DE10315571A1 (de) * | 2003-04-05 | 2004-10-14 | Merck Patent Gmbh | Pyrazolverbindungen |
| DE10315569A1 (de) * | 2003-04-05 | 2004-10-14 | Merck Patent Gmbh | Substituierte Pyrazolverbindungen |
| US20070093492A1 (en) * | 2004-03-09 | 2007-04-26 | Weir-Torn Jiaang | Pyrrolidine derivatives |
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- 2004-03-08 KR KR1020057018895A patent/KR20050119193A/ko not_active Withdrawn
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- 2004-03-08 PL PL377844A patent/PL377844A1/pl unknown
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2011
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Also Published As
| Publication number | Publication date |
|---|---|
| EP1626967A1 (de) | 2006-02-22 |
| JP4740115B2 (ja) | 2011-08-03 |
| CA2521201A1 (en) | 2004-10-21 |
| AU2004228120A1 (en) | 2004-10-21 |
| CN1768051A (zh) | 2006-05-03 |
| JP2006522035A (ja) | 2006-09-28 |
| AU2004228120B2 (en) | 2010-12-02 |
| AR043837A1 (es) | 2005-08-17 |
| WO2004089931A1 (de) | 2004-10-21 |
| JP2011148803A (ja) | 2011-08-04 |
| MXPA05010652A (es) | 2005-12-12 |
| PL377844A1 (pl) | 2006-02-20 |
| KR20050119193A (ko) | 2005-12-20 |
| DE10315572A1 (de) | 2004-10-14 |
| US20060264419A1 (en) | 2006-11-23 |
| BRPI0409164A (pt) | 2006-04-11 |
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