UA74787C2 - Respiratory syncytial virus replication inhibitors - Google Patents

Respiratory syncytial virus replication inhibitors Download PDF

Info

Publication number: UA74787C2
Authority: UA; Ukraine
Prior art keywords: formula; alkyl; methyl; pyridinyl; compounds
Prior art date: 1999-06-28

Application number

UA2002010360A

Other languages

English (en)

Ukrainian (uk)

Inventor

Kathleen Petrus Mari- Meersman

Koenraad Jozef Ludovik Andries

Original Assignee

Janssen Pharmaceutica Nv

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1999-06-28

Filing date

2000-06-20

Publication date

2006-02-15

2000-06-20 Application filed by Janssen Pharmaceutica Nv filed Critical Janssen Pharmaceutica Nv

2006-02-15 Publication of UA74787C2 publication Critical patent/UA74787C2/uk

Links

241000725643 Respiratory syncytial virus Species 0.000 title abstract description 6
239000003112 inhibitor Substances 0.000 title abstract 2
230000029812 viral genome replication Effects 0.000 title abstract 2
150000001875 compounds Chemical class 0.000 claims abstract description 356
-1 homopiperidinyl Chemical group 0.000 claims abstract description 118
239000000203 mixture Substances 0.000 claims abstract description 80
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 48
239000001257 hydrogen Substances 0.000 claims abstract description 47
150000003839 salts Chemical class 0.000 claims abstract description 32
125000001424 substituent group Chemical group 0.000 claims abstract description 32
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 28
125000003118 aryl group Chemical group 0.000 claims abstract description 26
150000001412 amines Chemical class 0.000 claims abstract description 21
239000003814 drug Substances 0.000 claims abstract description 18
238000002360 preparation method Methods 0.000 claims abstract description 18
239000002184 metal Chemical class 0.000 claims abstract description 14
229910052751 metal Inorganic materials 0.000 claims abstract description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 13
125000002911 monocyclic heterocycle group Chemical group 0.000 claims abstract description 12
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 12
239000000651 prodrug Substances 0.000 claims abstract description 12
229940002612 prodrug Drugs 0.000 claims abstract description 12
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract description 10
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 10
125000003386 piperidinyl group Chemical group 0.000 claims abstract description 9
125000004076 pyridyl group Chemical group 0.000 claims abstract description 9
125000003373 pyrazinyl group Chemical group 0.000 claims abstract description 5
125000002098 pyridazinyl group Chemical group 0.000 claims abstract description 5
125000000714 pyrimidinyl group Chemical group 0.000 claims abstract description 5
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 4
238000006243 chemical reaction Methods 0.000 claims description 76
125000000217 alkyl group Chemical group 0.000 claims description 53
239000002253 acid Substances 0.000 claims description 36
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 33
239000002585 base Substances 0.000 claims description 29
238000000034 method Methods 0.000 claims description 28
125000004432 carbon atom Chemical group C* 0.000 claims description 23
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 21
125000003545 alkoxy group Chemical group 0.000 claims description 14
230000000840 anti-viral effect Effects 0.000 claims description 14
229910052799 carbon Inorganic materials 0.000 claims description 14
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
125000006239 protecting group Chemical group 0.000 claims description 12
125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 11
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 9
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
239000003937 drug carrier Substances 0.000 claims description 8
208000036142 Viral infection Diseases 0.000 claims description 7
230000009385 viral infection Effects 0.000 claims description 7
239000008194 pharmaceutical composition Substances 0.000 claims description 6
239000004480 active ingredient Substances 0.000 claims description 5
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 5
238000005576 amination reaction Methods 0.000 claims description 5
125000000623 heterocyclic group Chemical group 0.000 claims description 5
231100000252 nontoxic Toxicity 0.000 claims description 5
230000003000 nontoxic effect Effects 0.000 claims description 5
239000003513 alkali Substances 0.000 claims description 4
239000003795 chemical substances by application Substances 0.000 claims description 4
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
125000004104 aryloxy group Chemical group 0.000 claims description 3
150000004696 coordination complex Chemical group 0.000 claims description 3
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
230000002265 prevention Effects 0.000 claims description 3
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
239000012458 free base Substances 0.000 claims description 2
125000002541 furyl group Chemical group 0.000 claims description 2
125000002883 imidazolyl group Chemical group 0.000 claims description 2
125000001786 isothiazolyl group Chemical group 0.000 claims description 2
125000000842 isoxazolyl group Chemical group 0.000 claims description 2
125000001715 oxadiazolyl group Chemical group 0.000 claims description 2
125000002971 oxazolyl group Chemical group 0.000 claims description 2
125000004193 piperazinyl group Chemical group 0.000 claims description 2
125000003226 pyrazolyl group Chemical group 0.000 claims description 2
125000000168 pyrrolyl group Chemical group 0.000 claims description 2
SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 2
125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 2
125000000335 thiazolyl group Chemical group 0.000 claims description 2
125000001544 thienyl group Chemical group 0.000 claims description 2
230000009466 transformation Effects 0.000 claims description 2
150000004684 trihydrates Chemical class 0.000 claims description 2
125000001475 halogen functional group Chemical group 0.000 claims 6
238000010306 acid treatment Methods 0.000 claims 1
125000003806 alkyl carbonyl amino group Chemical group 0.000 claims 1
229910052733 gallium Inorganic materials 0.000 claims 1
150000004682 monohydrates Chemical class 0.000 claims 1
229910052717 sulfur Inorganic materials 0.000 abstract description 8
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 abstract description 5
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 abstract 2
125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
125000000008 (C1-C10) alkyl group Chemical group 0.000 abstract 1
125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
150000001204 N-oxides Chemical class 0.000 abstract 1
125000004430 oxygen atom Chemical group O* 0.000 abstract 1
239000000543 intermediate Substances 0.000 description 221
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WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 36
239000012442 inert solvent Substances 0.000 description 32
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 31
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
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WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 24
239000003480 eluent Substances 0.000 description 24
125000005843 halogen group Chemical group 0.000 description 24
150000003254 radicals Chemical class 0.000 description 23
239000000741 silica gel Substances 0.000 description 23
229910002027 silica gel Inorganic materials 0.000 description 23
239000003054 catalyst Substances 0.000 description 22
150000002431 hydrogen Chemical class 0.000 description 22
239000000243 solution Substances 0.000 description 21
239000002244 precipitate Substances 0.000 description 20
238000004440 column chromatography Methods 0.000 description 19
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
229960004592 isopropanol Drugs 0.000 description 18
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 18
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
238000010511 deprotection reaction Methods 0.000 description 16
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 15
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 15
239000003638 chemical reducing agent Substances 0.000 description 15
208000015181 infectious disease Diseases 0.000 description 14
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
229940079593 drug Drugs 0.000 description 12
239000012044 organic layer Substances 0.000 description 12
229910052801 chlorine Inorganic materials 0.000 description 10
238000010992 reflux Methods 0.000 description 10
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
241000700605 Viruses Species 0.000 description 9
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 8
150000001298 alcohols Chemical class 0.000 description 8
125000001309 chloro group Chemical group Cl* 0.000 description 8
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 8
235000015320 potassium carbonate Nutrition 0.000 description 8
229930195734 saturated hydrocarbon Natural products 0.000 description 8
150000007513 acids Chemical class 0.000 description 7
229910021529 ammonia Inorganic materials 0.000 description 7
239000002552 dosage form Substances 0.000 description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
239000003826 tablet Substances 0.000 description 7
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 6
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
239000003153 chemical reaction reagent Substances 0.000 description 6
238000006722 reduction reaction Methods 0.000 description 6
239000012312 sodium hydride Substances 0.000 description 6
229910000104 sodium hydride Inorganic materials 0.000 description 6
239000000725 suspension Substances 0.000 description 6
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
239000011521 glass Substances 0.000 description 5
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
229910000041 hydrogen chloride Inorganic materials 0.000 description 5
239000003960 organic solvent Substances 0.000 description 5
239000011734 sodium Substances 0.000 description 5
239000007858 starting material Substances 0.000 description 5
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
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229910052784 alkaline earth metal Inorganic materials 0.000 description 4
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
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SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 3
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 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 description 3
229940126639 Compound 33 Drugs 0.000 description 3
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241000711920 Human orthopneumovirus Species 0.000 description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
PNUZDKCDAWUEGK-CYZMBNFOSA-N Sitafloxacin Chemical compound C([C@H]1N)N(C=2C(=C3C(C(C(C(O)=O)=CN3[C@H]3[C@H](C3)F)=O)=CC=2F)Cl)CC11CC1 PNUZDKCDAWUEGK-CYZMBNFOSA-N 0.000 description 3
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239000000443 aerosol Substances 0.000 description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
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230000003197 catalytic effect Effects 0.000 description 3
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229940125773 compound 10 Drugs 0.000 description 3
229940125797 compound 12 Drugs 0.000 description 3
229940125898 compound 5 Drugs 0.000 description 3
231100000135 cytotoxicity Toxicity 0.000 description 3
230000003013 cytotoxicity Effects 0.000 description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
230000000694 effects Effects 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
229910052731 fluorine Inorganic materials 0.000 description 3
238000002347 injection Methods 0.000 description 3
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239000012280 lithium aluminium hydride Substances 0.000 description 3
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ZZYXNRREDYWPLN-UHFFFAOYSA-N pyridine-2,3-diamine Chemical compound NC1=CC=CN=C1N ZZYXNRREDYWPLN-UHFFFAOYSA-N 0.000 description 1
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DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 1
OSDUDPQWLGJWGL-UHFFFAOYSA-N tert-butyl 4-(1h-benzimidazol-2-ylamino)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1NC1=NC2=CC=CC=C2N1 OSDUDPQWLGJWGL-UHFFFAOYSA-N 0.000 description 1
238000012360 testing method Methods 0.000 description 1
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
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239000003981 vehicle Substances 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
- 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
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Virology (AREA)
Oncology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Communicable Diseases (AREA)
Molecular Biology (AREA)
Pulmonology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Plural Heterocyclic Compounds (AREA)
Micro-Organisms Or Cultivation Processes Thereof (AREA)
Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

UA2002010360A 1999-06-28 2000-06-20 Respiratory syncytial virus replication inhibitors UA74787C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP99202088		1999-06-28
PCT/EP2000/005675 WO2001000612A2 (en)	1999-06-28	2000-06-20	Respiratory syncytial virus replication inhibitors

Publications (1)

Publication Number	Publication Date
UA74787C2 true UA74787C2 (en)	2006-02-15

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ID=8240373

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UA2002010360A UA74787C2 (en)	1999-06-28	2000-06-20	Respiratory syncytial virus replication inhibitors

Country Status (33)

Country	Link
US (3)	US6747028B1 (et)
EP (1)	EP1196409B1 (et)
JP (1)	JP2003503402A (et)
KR (1)	KR100731271B1 (et)
CN (1)	CN1210275C (et)
AR (1)	AR035991A1 (et)
AT (1)	ATE258928T1 (et)
AU (1)	AU778218B2 (et)
BG (1)	BG65328B1 (et)
BR (1)	BR0012047A (et)
CA (1)	CA2376676C (et)
DE (1)	DE60008112T2 (et)
DK (1)	DK1196409T3 (et)
EA (1)	EA005027B1 (et)
EE (1)	EE04591B1 (et)
ES (1)	ES2215683T3 (et)
HK (1)	HK1045997A1 (et)
HR (1)	HRP20010935A2 (et)
HU (1)	HUP0201869A3 (et)
IL (2)	IL147327A0 (et)
MX (1)	MXPA02000120A (et)
MY (1)	MY127687A (et)
NO (1)	NO322458B1 (et)
NZ (1)	NZ515664A (et)
PL (1)	PL200674B1 (et)
PT (1)	PT1196409E (et)
SI (1)	SI1196409T1 (et)
SK (1)	SK19122001A3 (et)
TR (1)	TR200103806T2 (et)
TW (1)	TWI278454B (et)
UA (1)	UA74787C2 (et)
WO (1)	WO2001000612A2 (et)
ZA (1)	ZA200110479B (et)

Families Citing this family (51)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6495580B1 (en)	1998-01-29	2002-12-17	Viropharma Incorporated	Compounds, compositions and methods for treating or preventing pneumovirus infection and associated diseases
EP1418175A1 (en) *	1999-06-28	2004-05-12	Janssen Pharmaceutica N.V.	Respiratory syncytial virus replication inhibitors
ATE258928T1 (de)	1999-06-28	2004-02-15	Janssen Pharmaceutica Nv	Respiratorisches syncytialvirus replikation inhibitoren
US6506738B1 (en)	2000-09-27	2003-01-14	Bristol-Myers Squibb Company	Benzimidazolone antiviral agents
US6774134B2 (en)	2000-12-20	2004-08-10	Bristol-Myers Squibb Company	Heterocyclic substituted 2-methyl-benzimidazole antiviral agents
US7030150B2 (en)	2001-05-11	2006-04-18	Trimeris, Inc.	Benzimidazole compounds and antiviral uses thereof
US6919331B2 (en)	2001-12-10	2005-07-19	Bristol-Myers Squibb Company	Substituted 2-methyl-benzimidazole respiratory syncytial virus antiviral agents
AU2003258176A1 (en)	2002-08-09	2004-02-25	Viropharma Incorporated	Compounds, compositions and methods for treating or preventing pneumovirus infection and associated diseases
WO2004014317A2 (en)	2002-08-09	2004-02-19	Viropharma Incorporated	Compounds, compositions and methods for treating or preventing pneumovirus infection and associated diseases
AU2003301436A1 (en) *	2002-10-17	2004-05-04	Amgen Inc.	Benzimidazole derivatives and their use as vanilloid receptor ligands
US7323567B2 (en)	2003-10-30	2008-01-29	Boehringer Ingelheim (Canada) Ltd.	RSV polymerase inhibitors
AR046972A1 (es) *	2003-12-18	2006-01-04	Tibotec Pharm Ltd	Derivados de los amino-bencimidazoles como inhibidores de la replicacion del virus sincitial respiratorio
JP2007514718A (ja)	2003-12-18	2007-06-07	テイボテク・フアーマシユーチカルズ・リミテツド	呼吸器シンシチウムウイルス複製のインヒビターとしてのアミノ−ベンズイミダゾール誘導体
AR046959A1 (es) *	2003-12-18	2006-01-04	Tibotec Pharm Ltd	Morfolinilo que contiene bencimidazoles como inhibidores de la replicacion del virus sincitial respiratorio
CN103450159A (zh)	2003-12-18	2013-12-18	泰博特克药品有限公司	作为呼吸道合胞病毒复制的抑制剂的哌啶-氨基-苯并咪唑类衍生物
TWI356055B (en) *	2003-12-18	2012-01-11	Tibotec Pharm Ltd	Aminobenzimidazoles and benzimidazoles as inhibito
MY142783A (en) *	2003-12-18	2010-12-31	Tibotec Pharm Ltd	5-or 6-substituted benzimidazole derivatives as inhibitors of respiratory syncytial virus replication
DE102004010207A1 (de) *	2004-03-02	2005-09-15	Aventis Pharma S.A.	Neue 4-Benzimidazol-2-yl-pyridazin-3-on-Derivate
MX2007011292A (es)	2005-03-17	2007-11-07	Tibotec Pharm Ltd	1,3-dihidro-bencimidazol-2-ilidenaminas como inhibidores de replicacion de virus respiratorios sinciciales.
US7884215B2 (en) *	2005-06-20	2011-02-08	Bonfanti Jean-Francois	2-substituted benzimidazoles
MX2007016537A (es)	2005-06-20	2008-03-06	Tibotec Pharm Ltd	1,3-dihidro-benzoimidazol-onas 1-(2-amino-3-(alquilo sustituido)-3h-bencimidazolilmetil)-3-sustituidas con actividad sobre virus respiratorios sinciciales.
WO2006136562A1 (en)	2005-06-20	2006-12-28	Tibotec Pharmaceuticals Ltd	Heterocyclylaminoalkyl substituted benzimidazoles
WO2011097607A1 (en) *	2010-02-08	2011-08-11	Southern Research Institute	Anti-viral treatment and assay to screen for anti-viral agent
TWI501967B (zh) *	2010-12-16	2015-10-01	Janssen R&D Ireland	作為呼吸道融合病毒抗病毒劑之氮雜吲哚類
TWI515187B (zh)	2010-12-16	2016-01-01	健生科學愛爾蘭無限公司	作為呼吸道融合病毒抗病毒劑之吲哚類
TWI527814B (zh)	2010-12-16	2016-04-01	健生科學愛爾蘭無限公司	作為呼吸道融合病毒抗病毒劑之氮雜苯并咪唑類
TWI530495B (zh)	2010-12-16	2016-04-21	健生科學愛爾蘭無限公司	苯并咪唑呼吸道融合病毒抑制劑
TWI541241B (zh) *	2010-12-16	2016-07-11	健生科學愛爾蘭無限公司	作為呼吸道融合病毒抗病毒劑之咪唑并吡啶類
DK3738434T3 (da)	2011-12-28	2023-12-04	Global Blood Therapeutics Inc	Mellemprodukter til opnåelse af substituerede benzaldehydforbindelser og fremgangsmåder til anvendelse deraf ved øgning af vævsoxygenering
WO2013102145A1 (en)	2011-12-28	2013-07-04	Global Blood Therapeutics, Inc.	Substituted heteroaryl aldehyde compounds and methods for their use in increasing tissue oxygenation
PL2864323T3 (pl)	2012-06-15	2017-09-29	Janssen Sciences Ireland Uc	Pochodne 1,3-dihydro-2h-benzoimidazol-2-onu podstawione heterocyklami jako środki przeciwwirusowe przeciwko wirusowi syncytium nabłonka oddechowego
US20140274961A1 (en)	2013-03-15	2014-09-18	Global Blood Therapeutics, Inc.	Compounds and uses thereof for the modulation of hemoglobin
US10100043B2 (en)	2013-03-15	2018-10-16	Global Blood Therapeutics, Inc.	Substituted aldehyde compounds and methods for their use in increasing tissue oxygenation
AU2014237330A1 (en)	2013-03-15	2015-09-17	Global Blood Therapeutics, Inc.	Compounds and uses thereof for the modulation of hemoglobin
US9422279B2 (en)	2013-03-15	2016-08-23	Global Blood Therapeutics, Inc.	Compounds and uses thereof for the modulation of hemoglobin
BR112015021982B1 (pt)	2013-03-15	2022-12-13	Global Blood Therapeutics, Inc	Compostos e seus usos para a modulação de hemoglobina
US9802900B2 (en)	2013-03-15	2017-10-31	Global Blood Therapeutics, Inc.	Bicyclic heteroaryl compounds and uses thereof for the modulation of hemoglobin
US9604999B2 (en)	2013-03-15	2017-03-28	Global Blood Therapeutics, Inc.	Compounds and uses thereof for the modulation of hemoglobin
KR102280614B1 (ko)	2013-03-15	2021-07-21	글로벌 블러드 테라퓨틱스, 인크.	헤모글로빈 조정을 위한 화합물 및 이의 용도
US10266551B2 (en)	2013-03-15	2019-04-23	Global Blood Therapeutics, Inc.	Compounds and uses thereof for the modulation of hemoglobin
US9458139B2 (en)	2013-03-15	2016-10-04	Global Blood Therapeutics, Inc.	Compounds and uses thereof for the modulation of hemoglobin
US8952171B2 (en)	2013-03-15	2015-02-10	Global Blood Therapeutics, Inc.	Compounds and uses thereof for the modulation of hemoglobin
EA201992707A1 (ru)	2013-11-18	2020-06-30	Глобал Блад Терапьютикс, Инк.	Соединения и их применения для модуляции гемоглобина
SI3102208T2 (sl)	2014-02-07	2024-10-30	Global Blood Therapeutics, Inc.	Kristalinični polimorf proste baze 2-hidroksi-6-((2-(1-izopropil-1H-pirazol-5-IL)piridin-3-IL)metoksi)- benzaldehida
JP2016079168A (ja)	2014-10-17	2016-05-16	塩野義製薬株式会社	９員縮合環誘導体
MA41841A (fr)	2015-03-30	2018-02-06	Global Blood Therapeutics Inc	Composés aldéhyde pour le traitement de la fibrose pulmonaire, de l'hypoxie, et de maladies auto-immunes et des tissus conjonctifs
US11020382B2 (en)	2015-12-04	2021-06-01	Global Blood Therapeutics, Inc.	Dosing regimens for 2-hydroxy-6-((2-(1-isopropyl-1h-pyrazol-5-yl)pyridin-3-yl)methoxy)benzaldehyde
AR108435A1 (es)	2016-05-12	2018-08-22	Global Blood Therapeutics Inc	Proceso para sintetizar 2-hidroxi-6-((2-(1-isopropil-1h-pirazol-5-il)-piridin-3-il)metoxi)benzaldehído
TWI778983B (zh)	2016-10-12	2022-10-01	美商全球血液治療公司	包含2-羥基-6-((2-(1-異丙基-1h-吡唑-5-基)吡啶-3-基)甲氧基)-苯甲醛之片劑
EP3860975B1 (en)	2018-10-01	2023-10-18	Global Blood Therapeutics, Inc.	Modulators of hemoglobin for the treatment of sickle cell disease
WO2021250180A1 (en)	2020-06-11	2021-12-16	Janssen Sciences Ireland Unlimited Company	Hemi (l)-tartrate forms of 3-({5-chloro-1-[3-(methylsulfonyl)propyl]-1h-indol-2 yl} methyl)-1-(2,2,2-trifluoroethyl)-1,3-dihydro-2h-imidazo[4,5-c]pyridin-2-one and pharmaceutical compositions comprising the same

Family Cites Families (20)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA1140119A (en)	1978-04-03	1983-01-25	Joseph Torremans	N-heterocyclyl-4-piperidinamines
US4556660A (en)	1982-07-12	1985-12-03	Janssen Pharmaceutica N.V.	N-(Bicyclic heterocyclyl)-4-piperidinamines
US4634704A (en)	1983-10-06	1987-01-06	Janssen Pharmaceutica, N.V.	Anti-allergic five membered heterocyclic ring containing N-(bicyclic heterocycyl)-4-piperidinamines
US4695569A (en)	1983-11-30	1987-09-22	Janssen Pharmaceutica N.V.	Bicyclic heterocyclyl containing N-(bicyclic heterocyclyl)-4-piperidinamines
EP0144101B1 (en)	1983-11-30	1991-02-06	Janssen Pharmaceutica N.V.	Bicyclic heterocyclyl containing n-(bicyclic heterocyclyl)-4-piperidinamines
PH23995A (en)	1984-01-09	1990-02-09	Janssen Pharmaceutica Nv	4((bicycle heterocyclyl)-methyl and hetero)piperidines
US4588722A (en)	1984-01-09	1986-05-13	Janssen Pharmaceutica N.V.	N-(4-piperidinyl) bicyclic condensed 2-imidazolamine derivatives
CA1327579C (en)	1986-02-03	1994-03-08	Frans Eduard Janssens	Anti-histaminic compositions containing n-heterocyclyl-4-piperidinamines
NZ223654A (en)	1987-03-09	1990-03-27	Janssen Pharmaceutica Nv	1-alkyl-substituted-benzimidazole-4-piperidinamines and pharmaceutical compositions
US4897401A (en)	1987-06-19	1990-01-30	Janssen Pharmaceutical N.V.	N-(4-piperidinyl) bicyclic condensed 2-imidazolamine derivatives useful in treating allergic diseases
CA1317939C (en) *	1987-07-01	1993-05-18	Janssen Pharmaceutica Naamloze Vennootschap	¬(bicyclic heterocyclyl)methyl and -hetero\| substituted hexahydro-1h-azepines and pyrrolidines
GB8716313D0 (en) *	1987-07-10	1987-08-19	Janssen Pharmaceutica Nv	2-(heterocyclylalkyl)imidazopyridines
US5360807A (en) *	1990-07-19	1994-11-01	Janssen Pharmaceutica N.V.	Substituted thiazolyl and substituted pyridinyl derivatives
NZ238863A (en) *	1990-07-19	1993-03-26	Janssen Pharmaceutica Nv	Substituted thiazolyl and pyridinyl derivatives
KR100190299B1 (ko)	1990-07-19	1999-06-01	디르크 반테	신규한 옥사졸릴 유도체
US5693661A (en)	1995-06-07	1997-12-02	Eli Lilly And Company	Anti-viral compounds
PE107598A1 (es)	1996-09-11	1999-01-29	Ucb Sa	Cetirizina util para el tratamiento de enfermedades de tipo virico
AU6031898A (en)	1997-01-22	1998-08-07	Eli Lilly And Company	Anti-viral compounds
AU7715198A (en)	1997-06-04	1998-12-21	Eli Lilly And Company	Anti-viral compounds
ATE258928T1 (de)	1999-06-28	2004-02-15	Janssen Pharmaceutica Nv	Respiratorisches syncytialvirus replikation inhibitoren

2000
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CA2376676A1 (en)	2001-01-04
BG65328B1 (bg)	2008-02-29
EA200200088A1 (ru)	2002-06-27
MY127687A (en)	2006-12-29
DE60008112D1 (en)	2004-03-11
DE60008112T2 (de)	2004-09-16
PT1196409E (pt)	2004-06-30
US20070015747A1 (en)	2007-01-18
PL352378A1 (en)	2003-08-25
SI1196409T1 (en)	2004-06-30
CA2376676C (en)	2009-01-20
CN1358181A (zh)	2002-07-10
EP1196409A2 (en)	2002-04-17
US20070135404A1 (en)	2007-06-14
ES2215683T3 (es)	2004-10-16
EE200100688A (et)	2003-04-15
US7528149B2 (en)	2009-05-05
HK1045997A1 (zh)	2002-12-20
US6747028B1 (en)	2004-06-08
US7179811B2 (en)	2007-02-20
JP2003503402A (ja)	2003-01-28
BG106286A (en)	2002-10-31
NZ515664A (en)	2004-01-30
CN1210275C (zh)	2005-07-13
AU5816600A (en)	2001-01-31
TWI278454B (en)	2007-04-11
BR0012047A (pt)	2002-03-12
MXPA02000120A (es)	2002-07-02
NO20016369D0 (no)	2001-12-27
NO20016369L (no)	2002-02-20
WO2001000612A3 (en)	2001-03-29
KR100731271B1 (ko)	2007-06-21
EP1196409B1 (en)	2004-02-04
ZA200110479B (en)	2003-03-20
HUP0201869A3 (en)	2003-12-29
EA005027B1 (ru)	2004-10-28
AU778218B2 (en)	2004-11-25
TR200103806T2 (tr)	2002-06-21
WO2001000612A2 (en)	2001-01-04
IL147327A (en)	2007-06-03
HRP20010935A2 (en)	2003-06-30
AR035991A1 (es)	2004-08-04
ATE258928T1 (de)	2004-02-15
NO322458B1 (no)	2006-10-09
DK1196409T3 (da)	2004-06-07
HUP0201869A2 (hu)	2002-11-28
SK19122001A3 (sk)	2003-01-09
EE04591B1 (et)	2006-02-15
KR20020003884A (ko)	2002-01-15
PL200674B1 (pl)	2009-01-30
IL147327A0 (en)	2002-08-14

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