ZA200100222B - Substituted pyrazole derivatives condensed with six-membered heterocyclic rings. - Google Patents
Substituted pyrazole derivatives condensed with six-membered heterocyclic rings. Download PDFInfo
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- ZA200100222B ZA200100222B ZA200100222A ZA200100222A ZA200100222B ZA 200100222 B ZA200100222 B ZA 200100222B ZA 200100222 A ZA200100222 A ZA 200100222A ZA 200100222 A ZA200100222 A ZA 200100222A ZA 200100222 B ZA200100222 B ZA 200100222B
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- South Africa
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- carbon atoms
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- 125000000623 heterocyclic group Chemical group 0.000 title claims description 28
- NOIXNOMHHWGUTG-UHFFFAOYSA-N 2-[[4-[4-pyridin-4-yl-1-(2,2,2-trifluoroethyl)pyrazol-3-yl]phenoxy]methyl]quinoline Chemical class C=1C=C(OCC=2N=C3C=CC=CC3=CC=2)C=CC=1C1=NN(CC(F)(F)F)C=C1C1=CC=NC=C1 NOIXNOMHHWGUTG-UHFFFAOYSA-N 0.000 title claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 246
- 150000001875 compounds Chemical class 0.000 claims description 127
- -1 azido, formyl Chemical group 0.000 claims description 107
- 125000000217 alkyl group Chemical group 0.000 claims description 103
- 125000002252 acyl group Chemical group 0.000 claims description 67
- 125000003545 alkoxy group Chemical group 0.000 claims description 63
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 59
- 229910052757 nitrogen Inorganic materials 0.000 claims description 56
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 53
- 229910052736 halogen Inorganic materials 0.000 claims description 53
- 150000002367 halogens Chemical class 0.000 claims description 53
- 229910052739 hydrogen Inorganic materials 0.000 claims description 53
- 239000001257 hydrogen Substances 0.000 claims description 49
- 125000003118 aryl group Chemical group 0.000 claims description 46
- 238000000034 method Methods 0.000 claims description 42
- 238000006243 chemical reaction Methods 0.000 claims description 39
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 37
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 31
- 125000005842 heteroatom Chemical group 0.000 claims description 29
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 29
- 229910052717 sulfur Inorganic materials 0.000 claims description 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
- 150000002431 hydrogen Chemical class 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 24
- 229920006395 saturated elastomer Polymers 0.000 claims description 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 21
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 16
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 16
- 229910052794 bromium Inorganic materials 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- ZOOGRGPOEVQQDX-KHLHZJAASA-N cyclic guanosine monophosphate Chemical compound C([C@H]1O2)O[P@](O)(=O)O[C@@H]1[C@H](O)[C@H]2N1C(N=C(NC2=O)N)=C2N=C1 ZOOGRGPOEVQQDX-KHLHZJAASA-N 0.000 claims description 15
- 239000003814 drug Substances 0.000 claims description 15
- 239000000460 chlorine Substances 0.000 claims description 14
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 14
- 238000011282 treatment Methods 0.000 claims description 14
- 125000002757 morpholinyl group Chemical group 0.000 claims description 13
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 13
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 12
- 125000004442 acylamino group Chemical group 0.000 claims description 12
- 125000004414 alkyl thio group Chemical group 0.000 claims description 12
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- 239000011737 fluorine Substances 0.000 claims description 12
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 230000009467 reduction Effects 0.000 claims description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- VVNCNSJFMMFHPL-VKHMYHEASA-N D-penicillamine Chemical group CC(C)(S)[C@@H](N)C(O)=O VVNCNSJFMMFHPL-VKHMYHEASA-N 0.000 claims description 10
- 150000001409 amidines Chemical class 0.000 claims description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
- 208000035475 disorder Diseases 0.000 claims description 10
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 10
- 150000002825 nitriles Chemical class 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 125000004076 pyridyl group Chemical group 0.000 claims description 10
- 125000001425 triazolyl group Chemical group 0.000 claims description 10
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 9
- 125000004193 piperazinyl group Chemical group 0.000 claims description 9
- 125000003386 piperidinyl group Chemical group 0.000 claims description 9
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 9
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- 125000004423 acyloxy group Chemical group 0.000 claims description 8
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- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
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- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 6
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- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 125000005041 acyloxyalkyl group Chemical group 0.000 claims description 4
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- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
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- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000005368 heteroarylthio group Chemical group 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 229940082615 organic nitrates used in cardiac disease Drugs 0.000 claims description 4
- 230000003647 oxidation Effects 0.000 claims description 4
- 238000007254 oxidation reaction Methods 0.000 claims description 4
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 4
- 206010020772 Hypertension Diseases 0.000 claims description 3
- 230000010933 acylation Effects 0.000 claims description 3
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- 230000015556 catabolic process Effects 0.000 claims description 3
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- 238000005660 chlorination reaction Methods 0.000 claims description 3
- 238000006731 degradation reaction Methods 0.000 claims description 3
- 150000002084 enol ethers Chemical class 0.000 claims description 3
- 230000009935 nitrosation Effects 0.000 claims description 3
- 238000007034 nitrosation reaction Methods 0.000 claims description 3
- 238000010534 nucleophilic substitution reaction Methods 0.000 claims description 3
- 125000006239 protecting group Chemical group 0.000 claims description 3
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 3
- KPKNTUUIEVXMOH-UHFFFAOYSA-N 1,4-dioxa-8-azaspiro[4.5]decane Chemical compound O1CCOC11CCNCC1 KPKNTUUIEVXMOH-UHFFFAOYSA-N 0.000 claims description 2
- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims description 2
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 2
- 201000001880 Sexual dysfunction Diseases 0.000 claims description 2
- 125000005333 aroyloxy group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 238000006555 catalytic reaction Methods 0.000 claims description 2
- AJXWEJAGUZJGRI-UHFFFAOYSA-N fluorine azide Chemical compound FN=[N+]=[N-] AJXWEJAGUZJGRI-UHFFFAOYSA-N 0.000 claims description 2
- 150000003948 formamides Chemical class 0.000 claims description 2
- 229940015043 glyoxal Drugs 0.000 claims description 2
- 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 claims description 2
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- 231100000872 sexual dysfunction Toxicity 0.000 claims description 2
- 230000009424 thromboembolic effect Effects 0.000 claims description 2
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims 2
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- 208000010125 myocardial infarction Diseases 0.000 description 1
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 230000036403 neuro physiology Effects 0.000 description 1
- 150000002829 nitrogen Chemical class 0.000 description 1
- 230000001129 nonadrenergic effect Effects 0.000 description 1
- 230000002536 noncholinergic effect Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 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
- 239000012038 nucleophile Substances 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 125000002347 octyl 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])[H] 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- QUANRIQJNFHVEU-UHFFFAOYSA-N oxirane;propane-1,2,3-triol Chemical compound C1CO1.OCC(O)CO QUANRIQJNFHVEU-UHFFFAOYSA-N 0.000 description 1
- 150000002941 palladium compounds Chemical class 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 230000018052 penile erection Effects 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- SONNWYBIRXJNDC-VIFPVBQESA-N phenylephrine Chemical compound CNC[C@H](O)C1=CC=CC(O)=C1 SONNWYBIRXJNDC-VIFPVBQESA-N 0.000 description 1
- 229960001802 phenylephrine Drugs 0.000 description 1
- 150000004031 phenylhydrazines Chemical class 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 230000035479 physiological effects, processes and functions Effects 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 210000004623 platelet-rich plasma Anatomy 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- LJCNRYVRMXRIQR-OLXYHTOASA-L potassium sodium L-tartrate Chemical compound [Na+].[K+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O LJCNRYVRMXRIQR-OLXYHTOASA-L 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004673 propylcarbonyl group Chemical group 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 210000002307 prostate Anatomy 0.000 description 1
- 229950003776 protoporphyrin Drugs 0.000 description 1
- 150000005229 pyrazolopyridines Chemical class 0.000 description 1
- ZZYXNRREDYWPLN-UHFFFAOYSA-N pyridine-2,3-diamine Chemical compound NC1=CC=CN=C1N ZZYXNRREDYWPLN-UHFFFAOYSA-N 0.000 description 1
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 230000004648 relaxation of smooth muscle Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 210000000329 smooth muscle myocyte Anatomy 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 1
- 239000001476 sodium potassium tartrate Substances 0.000 description 1
- 235000011006 sodium potassium tartrate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- UYCAUPASBSROMS-AWQJXPNKSA-M sodium;2,2,2-trifluoroacetate Chemical compound [Na+].[O-][13C](=O)[13C](F)(F)F UYCAUPASBSROMS-AWQJXPNKSA-M 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000011699 spontaneously hypertensive rat Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000000021 stimulant Substances 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 125000000101 thioether group Chemical group 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 229960003279 thiopental Drugs 0.000 description 1
- 230000002537 thrombolytic effect Effects 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical group OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- 241000701447 unidentified baculovirus Species 0.000 description 1
- 210000002229 urogenital system Anatomy 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 208000019553 vascular disease Diseases 0.000 description 1
- 230000001196 vasorelaxation Effects 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
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Classifications
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- 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
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
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- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- 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
-
- 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
-
- 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
- A61P9/12—Antihypertensives
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Reproductive Health (AREA)
- Gynecology & Obstetrics (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Urology & Nephrology (AREA)
- Pregnancy & Childbirth (AREA)
- Vascular Medicine (AREA)
- Endocrinology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19834044A DE19834044A1 (de) | 1998-07-29 | 1998-07-29 | Neue substituierte Pyrazolderivate |
Publications (1)
Publication Number | Publication Date |
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ZA200100222B true ZA200100222B (en) | 2001-08-07 |
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ID=7875637
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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ZA200100222A ZA200100222B (en) | 1998-07-29 | 2001-01-09 | Substituted pyrazole derivatives condensed with six-membered heterocyclic rings. |
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US (2) | US6743798B1 (zh) |
EP (1) | EP1102768B1 (zh) |
JP (1) | JP2002521483A (zh) |
KR (1) | KR20010085314A (zh) |
CN (1) | CN1165536C (zh) |
AR (1) | AR016736A1 (zh) |
AT (1) | ATE313543T1 (zh) |
AU (1) | AU751316B2 (zh) |
BG (1) | BG105177A (zh) |
BR (1) | BR9912562A (zh) |
CA (1) | CA2339071A1 (zh) |
CO (1) | CO5080799A1 (zh) |
DE (2) | DE19834044A1 (zh) |
ES (1) | ES2255288T3 (zh) |
HK (1) | HK1040712B (zh) |
HN (1) | HN1999000125A (zh) |
HU (1) | HUP0103815A3 (zh) |
ID (1) | ID28240A (zh) |
IL (1) | IL140584A0 (zh) |
MY (1) | MY133392A (zh) |
NO (1) | NO319073B1 (zh) |
NZ (1) | NZ509599A (zh) |
PE (1) | PE20000932A1 (zh) |
PL (1) | PL345675A1 (zh) |
RU (1) | RU2232161C2 (zh) |
SK (1) | SK1302001A3 (zh) |
SV (1) | SV1999000118A (zh) |
TR (1) | TR200100238T2 (zh) |
TW (1) | TW509691B (zh) |
WO (1) | WO2000006569A1 (zh) |
ZA (1) | ZA200100222B (zh) |
Families Citing this family (330)
Publication number | Priority date | Publication date | Assignee | Title |
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DE10054278A1 (de) * | 2000-11-02 | 2002-05-08 | Bayer Ag | Verwendung von Stimulatoren der löslichen Guanylatcyclase zur Behandlung von Osteoporose |
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WO2002042299A1 (de) * | 2000-11-22 | 2002-05-30 | Bayer Aktiengesellschaft | Neue lactam-substituierte pyrazolopyridinderivate |
DE10057754A1 (de) * | 2000-11-22 | 2002-05-23 | Bayer Ag | Neue Sulfonamid-substituierte Pyrazolopyridinderivate |
DE10057751A1 (de) * | 2000-11-22 | 2002-05-23 | Bayer Ag | Neue Carbamat-substituierte Pyrazolopyridinderivate |
DE10110747A1 (de) * | 2001-03-07 | 2002-09-12 | Bayer Ag | Substituierte 2,6-Diamino-3,5-dicyano-4-aryl-pyridine und ihre Verwendung |
DE10122894A1 (de) | 2001-05-11 | 2002-11-14 | Bayer Ag | Neue Sulfonat-substituierte Pyrazolopyridinderivate |
EP1267170A1 (en) * | 2001-06-07 | 2002-12-18 | Xzillion GmbH & CO.KG | Method for characterising polypeptides |
DE10132416A1 (de) * | 2001-07-04 | 2003-01-16 | Bayer Ag | Neue Morpholin-überbrückte Pyrazolopyridinderivate |
DE10220570A1 (de) | 2002-05-08 | 2003-11-20 | Bayer Ag | Carbamat-substituierte Pyrazolopyridine |
DE10222550A1 (de) * | 2002-05-17 | 2003-11-27 | Bayer Ag | Substituierte Benzyl-pyrazolopyridine |
DE10244810A1 (de) * | 2002-09-26 | 2004-04-08 | Bayer Ag | Neue Morpholin-überbrückte Indazolderivate |
EP1620428A1 (en) * | 2003-04-23 | 2006-02-01 | Pharmacia & Upjohn Company LLC | Substituted pyrimidinones and pyrimidinthiones as crf antagonists |
DE10351903A1 (de) * | 2003-11-06 | 2005-06-09 | Bayer Healthcare Ag | Neue Kombination |
DE102004042607A1 (de) * | 2004-09-03 | 2006-03-09 | Bayer Healthcare Ag | Substituierte Phenylaminothiazole und ihre Verwendung |
US20080138444A1 (en) * | 2004-10-05 | 2008-06-12 | Bayer Healthcare Ag | Method For Treating Bronchoconstriction and Pulmonary Vaso-Constriction |
WO2006056873A2 (en) * | 2004-11-29 | 2006-06-01 | Warner-Lambert Company Llc | Therapeutic pyrazolo[3,4-b] pyridines and indazoles |
DE102005031576A1 (de) * | 2005-07-06 | 2007-01-25 | Bayer Healthcare Ag | Verwendung von Aktivatoren der löslichen Guanylatzyklase zur Behandlung von Reperfusionsschäden |
DE102005031575A1 (de) * | 2005-07-06 | 2007-01-11 | Bayer Healthcare Ag | Verwendung von Aktivatoren der löslichen Guanylatzyklase zur Förderung der Wundheilung |
DE102005047945A1 (de) * | 2005-07-16 | 2007-01-18 | Bayer Healthcare Ag | Verwendung von Aktivatoren der löslichen Guanylatzyklase zur Behandlung von Raynaud Phänomenen |
AU2006272088A1 (en) * | 2005-07-18 | 2007-01-25 | Bayer Schering Pharma Aktiengesellschaft | Novel use of activators and stimulators of soluble guanylate cyclase for the prevention or treatment of renal disorders |
DE102005047946A1 (de) * | 2005-10-06 | 2007-05-03 | Bayer Healthcare Ag | Verwendung von Aktivatoren der löslichen Guanylatzyklase zur Behandlung von akuten und chronischen Lungenkrankheiten |
DE102006020327A1 (de) * | 2006-04-27 | 2007-12-27 | Bayer Healthcare Ag | Heterocyclisch substituierte, anellierte Pyrazol-Derivate und ihre Verwendung |
DE102006042143A1 (de) * | 2006-09-08 | 2008-03-27 | Bayer Healthcare Aktiengesellschaft | Neue substituierte Bipyridin-Derivate und ihre Verwendung |
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DE102006054757A1 (de) * | 2006-11-21 | 2008-05-29 | Bayer Healthcare Ag | Neue aza-bicyclische Verbindungen und ihre Verwendung |
DE102006056740A1 (de) * | 2006-12-01 | 2008-06-05 | Bayer Healthcare Ag | Cyclisch substituierte 3,5-Dicyano-2-thiopyridine und ihre Verwendung |
DE102006056739A1 (de) * | 2006-12-01 | 2008-06-05 | Bayer Healthcare Ag | Substituierte 4-Amino-3,5-dicyano-2-thiopyridine und ihre Verwendung |
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MX2009010122A (es) * | 2007-03-28 | 2009-10-19 | Neurosearch As | Derivados de purinilo y su uso como moduladores del canal de potasio. |
US20100105705A1 (en) * | 2007-03-28 | 2010-04-29 | Neurosearch A/S | Purinyl derivatives and their use as potassium channel modulators |
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US20100144864A1 (en) * | 2007-04-05 | 2010-06-10 | Ironwood Pharmaceuticals, Inc. | Soluble guanylate cyclase (sgc) modulators for treatment of lipid related disorders |
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DE102007019690A1 (de) | 2007-04-26 | 2008-10-30 | Bayer Healthcare Ag | Verwendung von cyclisch substituierten Furopyrimidin-Derivaten zur Behandlung der pulmonalen arteriellen Hypertonie |
RU2009145935A (ru) * | 2007-05-12 | 2011-06-20 | Байер Шеринг Фарма Акциенгезельшафт (DE) | Стимуляторы ргц, активаторы ргц и комбинации для лечения урологических нарушений |
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DE102007028407A1 (de) | 2007-06-20 | 2008-12-24 | Bayer Healthcare Ag | Substituierte Oxazolidinone und ihre Verwendung |
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DE102007028406A1 (de) | 2007-06-20 | 2008-12-24 | Bayer Healthcare Ag | Substituierte Oxazolidinone und ihre Verwendung |
DE102007028320A1 (de) | 2007-06-20 | 2008-12-24 | Bayer Healthcare Ag | Substituierte Oxazolidinone und ihre Verwendung |
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DE102007061766A1 (de) | 2007-12-20 | 2009-06-25 | Bayer Healthcare Ag | 4-(4-Cyano-2-thioaryl)-dihydropyrimidinone und ihre Verwendung |
DE102007061763A1 (de) | 2007-12-20 | 2009-06-25 | Bayer Healthcare Ag | Substituierte azabicyclische Verbindungen und ihre Verwendung |
DE102007061764A1 (de) | 2007-12-20 | 2009-06-25 | Bayer Healthcare Ag | Anellierte Cyanopyridine und ihre Verwendung |
DE102007061756A1 (de) | 2007-12-20 | 2009-06-25 | Bayer Healthcare Ag | Substituierte 4-Aminopyrimidin-5-carbonsäuren und ihre Verwendung |
DE102008052013A1 (de) | 2008-10-17 | 2010-04-22 | Bayer Schering Pharma Aktiengesellschaft | 4-(4-Cyano-2-thioaryl)-dihydropyrimidinone und ihre Verwendung |
DE102007061757A1 (de) | 2007-12-20 | 2009-06-25 | Bayer Healthcare Ag | Substituierte 2-Phenylpyrimidin-5-carbonsäuren und ihre Verwendung |
DE102008007400A1 (de) | 2008-02-04 | 2009-08-06 | Bayer Healthcare Ag | Substituierte Furane und ihre Verwendung |
DE102008013587A1 (de) * | 2008-03-11 | 2009-09-17 | Bayer Schering Pharma Aktiengesellschaft | Heteroaryl-substituierte Dicyanopyridine und ihre Verwendung |
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WO2023018795A1 (en) | 2021-08-11 | 2023-02-16 | Curtails Llc | Nep inhibitors for the treatment of laminitis |
AU2022429647A1 (en) | 2021-12-29 | 2024-07-04 | Bayer Aktiengesellschaft | Process for preparing (5s)-{[2-(4-carboxyphenyl)ethyl] |2-(2-{|3-chloro-4'-(trifluoromethyl)biphenyl-4- yl]methoxy}phenyl)ethyl]aminol-5,6,7,8-tetrahydroquinoline-2-carboxylic acid and its crystalline forms for use as pharmaceutically active compound |
TW202342034A (zh) | 2021-12-29 | 2023-11-01 | 德商拜耳廠股份有限公司 | 心肺病症之治療 |
AR128145A1 (es) | 2021-12-29 | 2024-03-27 | Bayer Ag | Formulación farmacéutica de polvo seco para inhalación y proceso de preparación |
ES2956054B2 (es) * | 2022-05-03 | 2024-07-01 | Moehs Iberica Sl | 2-(5-FLUORO-1-(2-FLUOROBENCIL)-1H-PIRAZOLO[3,4-b]PIRIDIN-3-IL)-5-NITROSOPIRIMIDIN-4,6-DIAMINA O UNA SAL DE LA MISMA, PROCEDIMIENTO PARA SU PREPARACION Y SU USO EN LA SINTESIS DE VERICIGUAT |
TW202412753A (zh) | 2022-06-09 | 2024-04-01 | 德商拜耳廠股份有限公司 | 用於治療女性心臟衰竭合併保留射出分率的可溶性鳥苷酸環化酶活化劑 |
WO2024086182A1 (en) | 2022-10-18 | 2024-04-25 | Tisento Therapeutics Inc. | Treatment of mitochondrial diseases with sgc stimulators |
WO2024086179A1 (en) | 2022-10-18 | 2024-04-25 | Tisento Therapeutics, Inc. | Pyrimidine sgc stimulators |
CN117924280B (zh) * | 2024-03-20 | 2024-07-12 | 中国人民解放军军事科学院军事医学研究院 | 取代噻吩基-5-氟-1h-吡唑并吡啶类化合物及其用途 |
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Publication number | Priority date | Publication date | Assignee | Title |
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DK27383A (da) | 1982-02-17 | 1983-08-18 | Lepetit Spa | Fremgangsmaade til fremstilling af pyrazol(4,3-c)pyridiner |
JP2928079B2 (ja) | 1994-02-14 | 1999-07-28 | 永信薬品工業股▲ふん▼有限公司 | 1−(置換ベンジル)−3−(置換アリール)縮合ピラゾール類、その製造法及びその用途 |
BR9712523A (pt) * | 1996-10-14 | 2000-05-09 | Bayer Ag | Novos derivados de pirazol heterociclilmetil-substituìdos |
DE19649460A1 (de) | 1996-11-26 | 1998-05-28 | Bayer Ag | Neue substituierte Pyrazolderivate |
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1998
- 1998-07-29 DE DE19834044A patent/DE19834044A1/de not_active Withdrawn
-
1999
- 1999-07-16 NZ NZ509599A patent/NZ509599A/en unknown
- 1999-07-16 HU HU0103815A patent/HUP0103815A3/hu unknown
- 1999-07-16 ID IDW20010237A patent/ID28240A/id unknown
- 1999-07-16 ES ES99938273T patent/ES2255288T3/es not_active Expired - Lifetime
- 1999-07-16 SK SK130-2001A patent/SK1302001A3/sk unknown
- 1999-07-16 RU RU2001105938/04A patent/RU2232161C2/ru not_active IP Right Cessation
- 1999-07-16 WO PCT/EP1999/005074 patent/WO2000006569A1/de not_active Application Discontinuation
- 1999-07-16 CN CNB99810504XA patent/CN1165536C/zh not_active Expired - Fee Related
- 1999-07-16 JP JP2000562371A patent/JP2002521483A/ja active Pending
- 1999-07-16 AU AU52840/99A patent/AU751316B2/en not_active Ceased
- 1999-07-16 IL IL14058499A patent/IL140584A0/xx unknown
- 1999-07-16 KR KR1020017001215A patent/KR20010085314A/ko not_active Application Discontinuation
- 1999-07-16 TR TR2001/00238T patent/TR200100238T2/xx unknown
- 1999-07-16 EP EP99938273A patent/EP1102768B1/de not_active Expired - Lifetime
- 1999-07-16 PL PL99345675A patent/PL345675A1/xx not_active Application Discontinuation
- 1999-07-16 DE DE59912966T patent/DE59912966D1/de not_active Expired - Lifetime
- 1999-07-16 US US09/744,830 patent/US6743798B1/en not_active Expired - Lifetime
- 1999-07-16 CA CA002339071A patent/CA2339071A1/en not_active Abandoned
- 1999-07-16 AT AT99938273T patent/ATE313543T1/de not_active IP Right Cessation
- 1999-07-16 BR BR9912562-5A patent/BR9912562A/pt not_active IP Right Cessation
- 1999-07-27 PE PE1999000749A patent/PE20000932A1/es not_active Application Discontinuation
- 1999-07-28 HN HN1999000125A patent/HN1999000125A/es unknown
- 1999-07-28 TW TW088112743A patent/TW509691B/zh not_active IP Right Cessation
- 1999-07-28 MY MYPI99003182A patent/MY133392A/en unknown
- 1999-07-29 AR ARP990103777A patent/AR016736A1/es not_active Application Discontinuation
- 1999-07-29 SV SV1999000118A patent/SV1999000118A/es not_active Application Discontinuation
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2001
- 2001-01-09 NO NO20010149A patent/NO319073B1/no not_active IP Right Cessation
- 2001-01-09 ZA ZA200100222A patent/ZA200100222B/en unknown
- 2001-01-24 BG BG105177A patent/BG105177A/xx unknown
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2002
- 2002-03-27 HK HK02102366.0A patent/HK1040712B/zh not_active IP Right Cessation
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2004
- 2004-05-28 US US10/856,153 patent/US20040224945A1/en not_active Abandoned
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