FI106716B - Menetelmä uusien terapeuttisesti käyttökelpoisten imidatso[2,3-b]pyridiini- ja bentsimidatsolijohdannaisten valmistamiseksi - Google Patents
Menetelmä uusien terapeuttisesti käyttökelpoisten imidatso[2,3-b]pyridiini- ja bentsimidatsolijohdannaisten valmistamiseksi Download PDFInfo
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- FI106716B FI106716B FI940659A FI940659A FI106716B FI 106716 B FI106716 B FI 106716B FI 940659 A FI940659 A FI 940659A FI 940659 A FI940659 A FI 940659A FI 106716 B FI106716 B FI 106716B
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title claims description 25
- 238000000034 method Methods 0.000 title claims description 21
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 title claims description 12
- 230000008569 process Effects 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title claims description 6
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 title claims description 5
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 63
- 125000003831 tetrazolyl group Chemical group 0.000 claims abstract description 8
- 239000002253 acid Substances 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- -1 preferably Chemical compound 0.000 claims description 13
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 12
- 150000007513 acids Chemical class 0.000 claims description 9
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- 230000007062 hydrolysis Effects 0.000 claims description 8
- 238000006460 hydrolysis reaction Methods 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 5
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 4
- 150000001735 carboxylic acids Chemical class 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 239000012442 inert solvent Substances 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 230000004913 activation Effects 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 239000007789 gas Substances 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
- 230000001681 protective effect Effects 0.000 claims description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 abstract description 6
- 239000003814 drug Substances 0.000 abstract description 4
- 239000004480 active ingredient Substances 0.000 abstract description 3
- 201000001320 Atherosclerosis Diseases 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 63
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 48
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 41
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 239000000203 mixture Substances 0.000 description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
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- 239000002904 solvent Substances 0.000 description 19
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
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- 101800000733 Angiotensin-2 Proteins 0.000 description 11
- CZGUSIXMZVURDU-JZXHSEFVSA-N Ile(5)-angiotensin II Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC=1C=CC=CC=1)C([O-])=O)NC(=O)[C@@H](NC(=O)[C@H](CCCNC(N)=[NH2+])NC(=O)[C@@H]([NH3+])CC([O-])=O)C(C)C)C1=CC=C(O)C=C1 CZGUSIXMZVURDU-JZXHSEFVSA-N 0.000 description 11
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 11
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 239000003480 eluent Substances 0.000 description 8
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- 230000005764 inhibitory process Effects 0.000 description 7
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 6
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
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- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 6
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- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 5
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
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- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229960005192 methoxamine Drugs 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 210000004877 mucosa Anatomy 0.000 description 1
- 210000000663 muscle cell Anatomy 0.000 description 1
- 230000002107 myocardial effect Effects 0.000 description 1
- QCCWVNLOJADEAV-UHFFFAOYSA-N n,n-dimethyl-1h-pyrrol-3-amine Chemical compound CN(C)C=1C=CNC=1 QCCWVNLOJADEAV-UHFFFAOYSA-N 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- YZMHQCWXYHARLS-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid Chemical class C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C21 YZMHQCWXYHARLS-UHFFFAOYSA-N 0.000 description 1
- 229940105631 nembutal Drugs 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000003305 oral gavage Methods 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- YOPKGUUNMWGPCZ-UHFFFAOYSA-N phosphoric acid;propane Chemical compound CCC.OP(O)(O)=O YOPKGUUNMWGPCZ-UHFFFAOYSA-N 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 210000001147 pulmonary artery Anatomy 0.000 description 1
- 238000004080 punching Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002287 radioligand Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 210000002254 renal artery Anatomy 0.000 description 1
- 230000036454 renin-angiotensin system Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000005201 scrubbing Methods 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 230000009870 specific binding Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 210000002820 sympathetic nervous system Anatomy 0.000 description 1
- 230000001360 synchronised effect Effects 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- VLKJJJUJOJNSKE-JKSUJKDBSA-N tert-butyl (1r,2r)-2-(4-methylphenyl)cyclohexane-1-carboxylate Chemical compound C1=CC(C)=CC=C1[C@H]1[C@H](C(=O)OC(C)(C)C)CCCC1 VLKJJJUJOJNSKE-JKSUJKDBSA-N 0.000 description 1
- CPKLXNJCDGSLKB-JKSUJKDBSA-N tert-butyl (1r,2r)-2-[4-(bromomethyl)phenyl]cyclohexane-1-carboxylate Chemical compound CC(C)(C)OC(=O)[C@@H]1CCCC[C@H]1C1=CC=C(CBr)C=C1 CPKLXNJCDGSLKB-JKSUJKDBSA-N 0.000 description 1
- 238000010257 thawing Methods 0.000 description 1
- 229960003279 thiopental Drugs 0.000 description 1
- 210000001042 thoracic artery Anatomy 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 208000019553 vascular disease Diseases 0.000 description 1
- 230000025033 vasoconstriction Effects 0.000 description 1
- 239000005526 vasoconstrictor agent Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
-
- 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
- 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)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4304455 | 1993-02-15 | ||
| DE4304455A DE4304455A1 (de) | 1993-02-15 | 1993-02-15 | Heterocyclisch substituierte Phenyl-cyclohexan-carbonsäurederivate |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI940659A0 FI940659A0 (fi) | 1994-02-11 |
| FI940659A7 FI940659A7 (fi) | 1994-08-16 |
| FI106716B true FI106716B (fi) | 2001-03-30 |
Family
ID=6480447
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI940659A FI106716B (fi) | 1993-02-15 | 1994-02-11 | Menetelmä uusien terapeuttisesti käyttökelpoisten imidatso[2,3-b]pyridiini- ja bentsimidatsolijohdannaisten valmistamiseksi |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US5395840A (enExample) |
| EP (1) | EP0611767B1 (enExample) |
| JP (1) | JPH06293741A (enExample) |
| KR (1) | KR940019708A (enExample) |
| CN (1) | CN1057085C (enExample) |
| AT (1) | ATE196141T1 (enExample) |
| AU (1) | AU672262B2 (enExample) |
| CA (1) | CA2115536C (enExample) |
| CZ (1) | CZ289096B6 (enExample) |
| DE (2) | DE4304455A1 (enExample) |
| DK (1) | DK0611767T3 (enExample) |
| ES (1) | ES2151908T3 (enExample) |
| FI (1) | FI106716B (enExample) |
| GR (1) | GR3034957T3 (enExample) |
| IL (1) | IL108625A (enExample) |
| MY (1) | MY131595A (enExample) |
| NO (1) | NO300810B1 (enExample) |
| NZ (1) | NZ250864A (enExample) |
| PH (1) | PH30172A (enExample) |
| PL (1) | PL177834B1 (enExample) |
| PT (1) | PT611767E (enExample) |
| RU (1) | RU2119480C1 (enExample) |
| SK (1) | SK15294A3 (enExample) |
| UA (1) | UA35574C2 (enExample) |
| ZA (1) | ZA94984B (enExample) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW300219B (enExample) * | 1991-09-14 | 1997-03-11 | Hoechst Ag | |
| HRP960015B1 (en) * | 1995-02-01 | 2000-12-31 | Bayer Ag | Substituted indole derivatives |
| DE19503160A1 (de) * | 1995-02-01 | 1996-08-08 | Bayer Ag | Verwendung von Phenylcyclohexylcarbonsäureamiden |
| DE19525028A1 (de) * | 1995-07-10 | 1997-01-16 | Bayer Ag | Amide und Sulfonamide von heterocyclisch substituierten Benzylaminen |
| JP2002507996A (ja) | 1997-07-03 | 2002-03-12 | デュポン ファーマシューティカルズ カンパニー | 神経学的障害を治療するためのイミダゾピリミジン類およびイミダゾピリジン類 |
| US6124463A (en) * | 1998-07-02 | 2000-09-26 | Dupont Pharmaceuticals | Benzimidazoles as corticotropin release factor antagonists |
| US6365589B1 (en) | 1998-07-02 | 2002-04-02 | Bristol-Myers Squibb Pharma Company | Imidazo-pyridines, -pyridazines, and -triazines as corticotropin releasing factor antagonists |
| AU755694B2 (en) * | 1998-11-17 | 2002-12-19 | Basf Aktiengesellschaft | 2-phenylbenzimidazoles and 2-phenylindoles, and production and use thereof |
| DE19924819A1 (de) * | 1999-05-29 | 2000-11-30 | Bayer Ag | Substituierte Phenylcyclohexancarbonsäurebenzylamid (Adenosinaufnahmeinhibitoren) |
| DE19924818A1 (de) * | 1999-05-29 | 2000-11-30 | Bayer Ag | Substituierte Phenylcyclohexancarbonsäureamide |
| DE10044792A1 (de) | 2000-09-11 | 2002-04-04 | Bayer Ag | Substituierte Phenylcyclohexancarbonsäureamide und ihre Verwendung |
| ES2443616T3 (es) | 2006-05-09 | 2014-02-19 | Mitsubishi Gas Chemical Company, Inc. | Procedimiento para la isomerización de alquilciclohexilbenceno |
| DK2442809T3 (en) | 2009-06-17 | 2016-12-19 | Vertex Pharma | Inhibitors of the replication of influenza virus |
| AU2011343642A1 (en) | 2010-12-16 | 2013-05-02 | Vertex Pharmaceuticals Incorporated | Inhibitors of influenza viruses replication |
| MY157429A (en) | 2011-06-24 | 2016-06-15 | Amgen Inc | Trpm8 antagonists and their use in treatments |
| JP2014517074A (ja) | 2011-06-24 | 2014-07-17 | アムジエン・インコーポレーテツド | Ｔｒｐｍ８アンタゴニストおよび治療におけるそれらの使用 |
| UA118010C2 (uk) | 2011-08-01 | 2018-11-12 | Вертекс Фармасьютікалз Інкорпорейтед | Інгібітори реплікації вірусів грипу |
| MD20140130A2 (ro) | 2012-06-29 | 2015-04-30 | Pfizer Inc. | 4-(amino-substituite)-7H-pirolo[2,3-d]pirimidine noi ca inhibitori de LRRK2 |
| US8952009B2 (en) | 2012-08-06 | 2015-02-10 | Amgen Inc. | Chroman derivatives as TRPM8 inhibitors |
| RS57541B1 (sr) | 2013-11-13 | 2018-10-31 | Vertex Pharma | Postupci za pripremu inhibitora replikacije virusa gripa |
| EP3068776B1 (en) | 2013-11-13 | 2019-05-29 | Vertex Pharmaceuticals Incorporated | Inhibitors of influenza viruses replication |
| WO2015092592A1 (en) | 2013-12-17 | 2015-06-25 | Pfizer Inc. | Novel 3,4-disubstituted-1h-pyrrolo[2,3-b]pyridines and 4,5-disubstituted-7h-pyrrolo[2,3-c]pyridazines as lrrk2 inhibitors |
| MA42422A (fr) | 2015-05-13 | 2018-05-23 | Vertex Pharma | Inhibiteurs de la réplication des virus de la grippe |
| JP6704416B2 (ja) | 2015-05-13 | 2020-06-03 | バーテックス ファーマシューティカルズ インコーポレイテッドＶｅｒｔｅｘ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｉｎｃｏｒｐｏｒａｔｅｄ | インフルエンザウイルスの複製の阻害剤を調製する方法 |
| CN108137586B (zh) | 2015-09-14 | 2021-04-13 | 辉瑞大药厂 | 作为LRRK2抑制剂的新颖咪唑并[4,5-c]喹啉和咪唑并[4,5-c][1,5]萘啶衍生物 |
| US20250109363A1 (en) * | 2022-03-08 | 2025-04-03 | Kj Chemicals Corporation | Composition containing highly safe amide compound |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5138069A (en) * | 1986-07-11 | 1992-08-11 | E. I. Du Pont De Nemours And Company | Angiotensin II receptor blocking imidazoles |
| IE64514B1 (en) * | 1989-05-23 | 1995-08-09 | Zeneca Ltd | Azaindenes |
| GB8911854D0 (en) * | 1989-05-23 | 1989-07-12 | Ici Plc | Heterocyclic compounds |
| US5164407A (en) * | 1989-07-03 | 1992-11-17 | Merck & Co., Inc. | Substituted imidazo-fused 5-membered ring heterocycles and their use as angiotensin ii antagonsists |
| ES2121773T3 (es) * | 1990-06-08 | 1998-12-16 | Hoechst Marion Roussel Inc | Derivados de bencimidazol, su procedimiento de preparacion, productos intermedios, su aplicacion como medicamentos y composiciones farmaceuticas que los contienen. |
| RU1836357C (ru) * | 1990-07-23 | 1993-08-23 | Др.Карл Томэ ГмбХ | Производные бензимидазола, их изомеры, смеси изомеров, гидраты или их физиологически переносимые соли, обладающие антагонистическими в отношении ангиотензина свойствами |
| EP0470543A1 (de) * | 1990-08-10 | 1992-02-12 | Dr. Karl Thomae GmbH | Heterocyclische Imidazole, diese Verbindungen enthaltende Arzneimittel und Verfahren zur ihrer Herstellung |
| DE4031635A1 (de) * | 1990-10-05 | 1992-04-09 | Thomae Gmbh Dr K | Substituierte 1-benzyl-benzimidazole, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
| DE4224133A1 (de) * | 1992-07-22 | 1994-01-27 | Thomae Gmbh Dr K | Benzimidazole, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung |
| DE4200954A1 (de) * | 1991-04-26 | 1992-10-29 | Bayer Ag | Heterocyclisch substituierte phenylessigsaeurederivate |
-
1993
- 1993-02-15 DE DE4304455A patent/DE4304455A1/de not_active Withdrawn
-
1994
- 1994-01-31 AU AU54807/94A patent/AU672262B2/en not_active Ceased
- 1994-02-02 ES ES94101543T patent/ES2151908T3/es not_active Expired - Lifetime
- 1994-02-02 DK DK94101543T patent/DK0611767T3/da active
- 1994-02-02 PT PT94101543T patent/PT611767E/pt unknown
- 1994-02-02 DE DE59409509T patent/DE59409509D1/de not_active Expired - Fee Related
- 1994-02-02 EP EP94101543A patent/EP0611767B1/de not_active Expired - Lifetime
- 1994-02-02 AT AT94101543T patent/ATE196141T1/de not_active IP Right Cessation
- 1994-02-08 US US08/193,835 patent/US5395840A/en not_active Expired - Fee Related
- 1994-02-09 SK SK152-94A patent/SK15294A3/sk unknown
- 1994-02-11 PL PL94302213A patent/PL177834B1/pl unknown
- 1994-02-11 NZ NZ250864A patent/NZ250864A/en unknown
- 1994-02-11 IL IL108625A patent/IL108625A/xx not_active IP Right Cessation
- 1994-02-11 CA CA002115536A patent/CA2115536C/en not_active Expired - Fee Related
- 1994-02-11 UA UA94005092A patent/UA35574C2/uk unknown
- 1994-02-11 FI FI940659A patent/FI106716B/fi active
- 1994-02-14 ZA ZA94984A patent/ZA94984B/xx unknown
- 1994-02-14 PH PH47762A patent/PH30172A/en unknown
- 1994-02-14 JP JP6037543A patent/JPH06293741A/ja active Pending
- 1994-02-14 MY MYPI94000321A patent/MY131595A/en unknown
- 1994-02-14 RU RU94004975A patent/RU2119480C1/ru active
- 1994-02-14 KR KR1019940002533A patent/KR940019708A/ko not_active Abandoned
- 1994-02-14 NO NO940506A patent/NO300810B1/no not_active IP Right Cessation
- 1994-02-15 CZ CZ1994329A patent/CZ289096B6/cs not_active IP Right Cessation
- 1994-02-15 CN CN94101553A patent/CN1057085C/zh not_active Expired - Fee Related
-
2000
- 2000-11-30 GR GR20000402660T patent/GR3034957T3/el not_active IP Right Cessation
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