PH26670A - Novel pyridazinamine derivative - Google Patents

Novel pyridazinamine derivative Download PDF

Info

Publication number: PH26670A
Authority: PH; Philippines
Prior art keywords: parts; formula; residue; hydrogen; galkyl
Prior art date: 1987-11-23

Application number

PH37851A

Other languages

English (en)

Inventor

Raymond A Stokbroekx

Marcel J M Van Der Aa

Marcel G M Luyckx

Gilbert A J Grauwels

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.)

1987-11-23

Filing date

1988-11-23

Publication date

1992-09-15

1988-11-23 Application filed by Janssen Pharmaceutica Nv filed Critical Janssen Pharmaceutica Nv

1992-09-15 Publication of PH26670A publication Critical patent/PH26670A/en

Links

LETVJWLLIMJADE-UHFFFAOYSA-N pyridazin-3-amine Chemical class NC1=CC=CN=N1 LETVJWLLIMJADE-UHFFFAOYSA-N 0.000 title abstract description 4
150000001875 compounds Chemical class 0.000 claims abstract description 109
-1 hydroxy, mercapto Chemical class 0.000 claims abstract description 89
239000001257 hydrogen Substances 0.000 claims abstract description 54
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 54
238000000034 method Methods 0.000 claims abstract description 40
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 33
239000002253 acid Substances 0.000 claims abstract description 32
150000002431 hydrogen Chemical class 0.000 claims abstract description 20
230000000840 anti-viral effect Effects 0.000 claims abstract description 19
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 14
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 13
229910052717 sulfur Inorganic materials 0.000 claims abstract description 9
239000004480 active ingredient Substances 0.000 claims abstract description 8
125000001475 halogen functional group Chemical group 0.000 claims abstract 8
239000000203 mixture Substances 0.000 claims description 132
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 43
229920000858 Cyclodextrin Polymers 0.000 claims description 36
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 24
HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 claims description 23
241000700605 Viruses Species 0.000 claims description 12
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
125000001424 substituent group Chemical group 0.000 claims description 8
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 7
241001465754 Metazoa Species 0.000 claims description 5
238000011200 topical administration Methods 0.000 claims description 5
238000007910 systemic administration Methods 0.000 claims description 4
230000009885 systemic effect Effects 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
108091008771 Rev-ErbA proteins Proteins 0.000 claims 1
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims 1
150000003839 salts Chemical class 0.000 abstract description 40
239000008194 pharmaceutical composition Substances 0.000 abstract description 12
125000003118 aryl group Chemical group 0.000 abstract description 10
229910052760 oxygen Inorganic materials 0.000 abstract description 8
125000004104 aryloxy group Chemical group 0.000 abstract description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 4
239000003443 antiviral agent Substances 0.000 abstract description 3
125000005135 aryl sulfinyl group Chemical group 0.000 abstract description 2
125000005110 aryl thio group Chemical group 0.000 abstract description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 abstract 1
125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 abstract 1
125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 abstract 1
125000006700 (C1-C6) alkylthio group Chemical group 0.000 abstract 1
125000006619 (C1-C6) dialkylamino group Chemical group 0.000 abstract 1
229940121357 antivirals Drugs 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 144
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150000003254 radicals Chemical class 0.000 description 42
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239000000284 extract Substances 0.000 description 29
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238000001816 cooling Methods 0.000 description 26
239000000706 filtrate Substances 0.000 description 25
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 25
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239000002904 solvent Substances 0.000 description 20
125000005843 halogen group Chemical group 0.000 description 19
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
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239000000741 silica gel Substances 0.000 description 18
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KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 17
239000012044 organic layer Substances 0.000 description 16
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
229910000029 sodium carbonate Inorganic materials 0.000 description 15
239000002585 base Substances 0.000 description 12
125000004356 hydroxy functional group Chemical group O* 0.000 description 11
238000007126 N-alkylation reaction Methods 0.000 description 10
239000003795 chemical substances by application Substances 0.000 description 10
229940097362 cyclodextrins Drugs 0.000 description 10
239000012442 inert solvent Substances 0.000 description 10
229910052751 metal Inorganic materials 0.000 description 10
239000002184 metal Substances 0.000 description 10
PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 10
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ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 9
150000007513 acids Chemical class 0.000 description 9
238000005804 alkylation reaction Methods 0.000 description 9
125000004432 carbon atom Chemical group C* 0.000 description 9
150000002576 ketones Chemical class 0.000 description 9
239000007858 starting material Substances 0.000 description 9
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 9
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 8
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
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YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 8
150000001412 amines Chemical class 0.000 description 8
239000003153 chemical reaction reagent Substances 0.000 description 8
150000002148 esters Chemical class 0.000 description 8
239000010410 layer Substances 0.000 description 8
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239000003921 oil Substances 0.000 description 8
235000019198 oils Nutrition 0.000 description 8
229910000027 potassium carbonate Inorganic materials 0.000 description 8
150000001266 acyl halides Chemical class 0.000 description 7
FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 7
229940093499 ethyl acetate Drugs 0.000 description 7
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QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
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125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
GUDMZGLFZNLYEY-UHFFFAOYSA-N cyclopropylmethanol Chemical compound OCC1CC1 GUDMZGLFZNLYEY-UHFFFAOYSA-N 0.000 description 1
NUOUOKKFHOLVIW-UHFFFAOYSA-N cyclopropylmethyl 4-[2-[1-(6-chloropyridazin-3-yl)piperidin-4-yl]ethoxy]benzoate Chemical compound N1=NC(Cl)=CC=C1N1CCC(CCOC=2C=CC(=CC=2)C(=O)OCC2CC2)CC1 NUOUOKKFHOLVIW-UHFFFAOYSA-N 0.000 description 1
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230000002939 deleterious effect Effects 0.000 description 1
238000000151 deposition Methods 0.000 description 1
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HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
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XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
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125000004185 ester group Chemical group 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
CYPXEPWPTXKUPL-UHFFFAOYSA-N ethyl 1-benzylpyrrolidine-3-carboxylate Chemical compound C1C(C(=O)OCC)CCN1CC1=CC=CC=C1 CYPXEPWPTXKUPL-UHFFFAOYSA-N 0.000 description 1
YOOWDGFRUIVYAH-UHFFFAOYSA-N ethyl 2-[4-(2-piperidin-4-ylethoxy)phenyl]acetate Chemical compound C1=CC(CC(=O)OCC)=CC=C1OCCC1CCNCC1 YOOWDGFRUIVYAH-UHFFFAOYSA-N 0.000 description 1
UCFHJQFPGXNALY-UHFFFAOYSA-N ethyl 2-[4-(3-piperidin-4-ylpropoxy)phenyl]acetate Chemical compound C1=CC(CC(=O)OCC)=CC=C1OCCCC1CCNCC1 UCFHJQFPGXNALY-UHFFFAOYSA-N 0.000 description 1
LUSHYPLDRVACQI-UHFFFAOYSA-N ethyl 3-(1-benzylpiperidin-4-yl)propanoate Chemical compound C1CC(CCC(=O)OCC)CCN1CC1=CC=CC=C1 LUSHYPLDRVACQI-UHFFFAOYSA-N 0.000 description 1
HPINOMFYMUAFCZ-UHFFFAOYSA-N ethyl 3-(2-ethoxy-2-oxoethyl)-8-azabicyclo[3.2.1]octane-8-carboxylate Chemical compound C1C(CC(=O)OCC)CC2CCC1N2C(=O)OCC HPINOMFYMUAFCZ-UHFFFAOYSA-N 0.000 description 1
ZEIFBQQAAWWUAI-UHFFFAOYSA-N ethyl 3-(2-hydroxyethyl)-8-azabicyclo[3.2.1]octane-8-carboxylate Chemical compound C1C(CCO)CC2CCC1N2C(=O)OCC ZEIFBQQAAWWUAI-UHFFFAOYSA-N 0.000 description 1
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MWSMNBYIEBRXAL-UHFFFAOYSA-N ethyl 3-hydroxybenzoate Chemical compound CCOC(=O)C1=CC=CC(O)=C1 MWSMNBYIEBRXAL-UHFFFAOYSA-N 0.000 description 1
NUPLANHIUNUPQC-UHFFFAOYSA-N ethyl 4-(2-hydroxyethyl)piperidine-1-carboxylate Chemical compound CCOC(=O)N1CCC(CCO)CC1 NUPLANHIUNUPQC-UHFFFAOYSA-N 0.000 description 1
FTSHBKRKWKZGFZ-UHFFFAOYSA-N ethyl 4-(2-piperidin-4-ylethoxy)benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1OCCC1CCNCC1 FTSHBKRKWKZGFZ-UHFFFAOYSA-N 0.000 description 1
FADPTWZEJSVNRI-UHFFFAOYSA-N ethyl 4-(2-piperidin-4-ylpropoxy)benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1OCC(C)C1CCNCC1 FADPTWZEJSVNRI-UHFFFAOYSA-N 0.000 description 1
YFNSVTKRYJNZKK-UHFFFAOYSA-N ethyl 4-(3-hydroxypropyl)piperidine-1-carboxylate Chemical compound CCOC(=O)N1CCC(CCCO)CC1 YFNSVTKRYJNZKK-UHFFFAOYSA-N 0.000 description 1
PGKWGMSAHDORQF-UHFFFAOYSA-N ethyl 4-(3-piperidin-4-ylpropoxy)benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1OCCCC1CCNCC1 PGKWGMSAHDORQF-UHFFFAOYSA-N 0.000 description 1
YRCQFIFDSGTRCA-UHFFFAOYSA-N ethyl 4-(4-hydroxybutyl)piperidine-1-carboxylate Chemical compound CCOC(=O)N1CCC(CCCCO)CC1 YRCQFIFDSGTRCA-UHFFFAOYSA-N 0.000 description 1
RFMPTFWIPCXJPE-UHFFFAOYSA-N ethyl 4-[(1-benzyl-4-hydroxypiperidin-4-yl)methoxy]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1OCC1(O)CCN(CC=2C=CC=CC=2)CC1 RFMPTFWIPCXJPE-UHFFFAOYSA-N 0.000 description 1
QKBHTYSMZNEBLM-UHFFFAOYSA-N ethyl 4-[(4-hydroxypiperidin-4-yl)methoxy]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1OCC1(O)CCNCC1 QKBHTYSMZNEBLM-UHFFFAOYSA-N 0.000 description 1
FPAMFYXOSCXWRI-UHFFFAOYSA-N ethyl 4-[2-(1-pyridazin-3-ylpiperidin-4-yl)ethoxy]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1OCCC1CCN(C=2N=NC=CC=2)CC1 FPAMFYXOSCXWRI-UHFFFAOYSA-N 0.000 description 1
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125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
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239000001294 propane Substances 0.000 description 1
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239000000375 suspending agent Substances 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/50—Pyridazines; Hydrogenated pyridazines
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D237/20—Nitrogen atoms
- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Medicinal Chemistry (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Virology (AREA)
Oncology (AREA)
Communicable Diseases (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Pyrrole Compounds (AREA)
Hydrogenated Pyridines (AREA)

PH37851A 1987-11-23 1988-11-23 Novel pyridazinamine derivative PH26670A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US12453087A	1987-11-23	1987-11-23

Publications (1)

Publication Number	Publication Date
PH26670A true PH26670A (en)	1992-09-15

Family

ID=22415413

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
PH37851A PH26670A (en)	1987-11-23	1988-11-23	Novel pyridazinamine derivative

Country Status (26)

Country	Link
EP (1)	EP0320032B1 (es)
JP (1)	JPH0629255B2 (es)
KR (1)	KR0125280B1 (es)
CN (1)	CN1021328C (es)
AT (1)	ATE117296T1 (es)
AU (1)	AU611504B2 (es)
BG (1)	BG60676B1 (es)
CA (1)	CA1327573C (es)
DE (1)	DE3852816T2 (es)
DK (1)	DK651288A (es)
ES (1)	ES2070126T3 (es)
FI (1)	FI92584C (es)
GR (1)	GR3015816T3 (es)
HU (1)	HU200762B (es)
IE (1)	IE65768B1 (es)
IL (1)	IL88429A (es)
JO (1)	JO1552B1 (es)
MA (1)	MA21446A1 (es)
MY (1)	MY104343A (es)
NO (1)	NO171980C (es)
NZ (1)	NZ226920A (es)
PH (1)	PH26670A (es)
PT (1)	PT89047B (es)
SU (1)	SU1724013A3 (es)
TN (1)	TNSN88128A1 (es)
ZA (1)	ZA888744B (es)

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JP4544999B2 (ja) *	2002-11-25	2010-09-15	持田製薬株式会社	４−ヒドロキシピペリジン誘導体を有効成分とする呼吸器疾患治療剤
PL1648874T3 (pl)	2003-07-30	2012-04-30	Xenon Pharmaceuticals Inc	Pochodne piperazyny i ich zastosowanie jako środków leczniczych
US7759348B2 (en)	2003-07-30	2010-07-20	Xenon Pharmaceuticals Inc.	Pyridazine derivatives and their use as therapeutic agents
US7754711B2 (en) *	2003-07-30	2010-07-13	Xenon Pharmaceuticals Inc.	Pyridazine derivatives and their use as therapeutic agents
CA2533897A1 (en) *	2003-07-30	2005-02-10	Xenon Pharmaceuticals Inc.	Pyridazine derivatives and their use as therapeutic agents
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BRPI0515482A (pt)	2004-09-20	2008-07-22	Xenon Pharmaceuticals Inc	derivados heterocìclicos e seus usos como agentes terapêuticos
MX2007003332A (es)	2004-09-20	2007-06-05	Xenon Pharmaceuticals Inc	Derivados heterociclicos y su uso como inhibidores de estearoil-coa-desaturasa.
CN101084211A (zh)	2004-09-20	2007-12-05	泽农医药公司	杂环衍生物及其作为治疗剂的用途
BRPI0515500A (pt)	2004-09-20	2008-07-29	Xenon Pharmaceuticals Inc	derivados piridazina para inibição de estearoil-coa-desaturase
MX2007003318A (es)	2004-09-20	2007-05-18	Xenon Pharmaceuticals Inc	Derivados heterociclicos y su uso como agentes terapeuticos.
AU2005286647A1 (en)	2004-09-20	2006-03-30	Xenon Pharmaceuticals Inc.	Heterocyclic derivatives and their use as stearoyl-CoA desaturase inhibitors
AU2005286728A1 (en)	2004-09-20	2006-03-30	Xenon Pharmaceuticals Inc.	Heterocyclic derivatives and their use as mediators of stearoyl-CoA desaturase
CA2618646A1 (en)	2005-06-03	2007-11-15	Xenon Pharmaceuticals Inc.	Aminothiazole derivatives as human stearoyl-coa desaturase inhibitors
MX2007016508A (es) *	2005-06-30	2008-03-04	Prosidion Ltd	Agonistas del receptor acoplado a la proteina g.
CN1887875B (zh) *	2005-06-30	2011-04-06	深圳市东阳光实业发展有限公司	哒嗪胺衍生物及其用于制备小rna病毒抑制剂的用途
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EP2402324A1 (en)	2006-05-29	2012-01-04	High Point Pharmaceuticals, LLC	Benzodioxolylcyclopropylpiperazinylpyridazines
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CN101864003B (zh) *	2010-06-11	2012-05-02	漆又毛	一种6-脱氧硫醚氨基酸环糊精衍生物的合成方法
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1988
- 1988-10-26 MY MYPI88001214A patent/MY104343A/en unknown
- 1988-11-02 CA CA000581965A patent/CA1327573C/en not_active Expired - Fee Related
- 1988-11-09 NZ NZ226920A patent/NZ226920A/xx unknown
- 1988-11-17 DE DE3852816T patent/DE3852816T2/de not_active Expired - Fee Related
- 1988-11-17 EP EP88202572A patent/EP0320032B1/en not_active Expired - Lifetime
- 1988-11-17 ES ES88202572T patent/ES2070126T3/es not_active Expired - Lifetime
- 1988-11-17 AT AT88202572T patent/ATE117296T1/de not_active IP Right Cessation
- 1988-11-18 AU AU25751/88A patent/AU611504B2/en not_active Ceased
- 1988-11-21 IL IL88429A patent/IL88429A/xx not_active IP Right Cessation
- 1988-11-21 TN TNTNSN88128A patent/TNSN88128A1/fr unknown
- 1988-11-21 BG BG86132A patent/BG60676B1/bg unknown
- 1988-11-22 DK DK651288A patent/DK651288A/da not_active Application Discontinuation
- 1988-11-22 JP JP63293739A patent/JPH0629255B2/ja not_active Expired - Fee Related
- 1988-11-22 PT PT89047A patent/PT89047B/pt not_active IP Right Cessation
- 1988-11-22 MA MA21689A patent/MA21446A1/fr unknown
- 1988-11-22 HU HU885991A patent/HU200762B/hu not_active IP Right Cessation
- 1988-11-22 FI FI885409A patent/FI92584C/fi not_active IP Right Cessation
- 1988-11-22 ZA ZA888744A patent/ZA888744B/xx unknown
- 1988-11-22 NO NO885190A patent/NO171980C/no unknown
- 1988-11-22 SU SU884356881A patent/SU1724013A3/ru active
- 1988-11-22 JO JO19881552A patent/JO1552B1/en active
- 1988-11-22 IE IE348688A patent/IE65768B1/en not_active IP Right Cessation
- 1988-11-23 CN CN88108173A patent/CN1021328C/zh not_active Expired - Fee Related
- 1988-11-23 PH PH37851A patent/PH26670A/en unknown
- 1988-11-23 KR KR1019880015415A patent/KR0125280B1/ko not_active Expired - Fee Related
1995
- 1995-04-17 GR GR950400946T patent/GR3015816T3/el unknown

Also Published As

Publication number	Publication date
ATE117296T1 (de)	1995-02-15
DE3852816T2 (de)	1995-06-08
NO171980C (no)	1993-05-26
TNSN88128A1 (fr)	1990-07-10
IE883486L (en)	1989-05-23
BG86132A (bg)	1993-12-24
IE65768B1 (en)	1995-11-15
PT89047A (pt)	1988-12-01
JPH01207278A (ja)	1989-08-21
NO171980B (no)	1993-02-15
AU611504B2 (en)	1991-06-13
BG60676B1 (bg)	1995-12-29
DK651288D0 (da)	1988-11-22
IL88429A (en)	1993-05-13
NO885190D0 (no)	1988-11-22
NZ226920A (en)	1990-06-26
KR890008126A (ko)	1989-07-08
CN1021328C (zh)	1993-06-23
JPH0629255B2 (ja)	1994-04-20
GR3015816T3 (en)	1995-07-31
DE3852816D1 (de)	1995-03-02
ES2070126T3 (es)	1995-06-01
MY104343A (en)	1994-03-31
FI885409A0 (fi)	1988-11-22
EP0320032A1 (en)	1989-06-14
HUT48617A (en)	1989-06-28
KR0125280B1 (ko)	1997-12-05
CA1327573C (en)	1994-03-08
ZA888744B (en)	1990-07-25
SU1724013A3 (ru)	1992-03-30
AU2575188A (en)	1989-05-25
CN1033274A (zh)	1989-06-07
EP0320032B1 (en)	1995-01-18
HU200762B (en)	1990-08-28
IL88429A0 (en)	1989-06-30
FI885409A7 (fi)	1989-05-24
DK651288A (da)	1989-05-24
JO1552B1 (en)	1989-12-16
FI92584C (fi)	1994-12-12
NO885190L (no)	1989-05-24
PT89047B (pt)	1993-03-31
MA21446A1 (fr)	1989-07-01
FI92584B (fi)	1994-08-31

Publication	Publication Date	Title
PH26670A (en)	1992-09-15	Novel pyridazinamine derivative
US4992433A (en)	1991-02-12	Novel pyridazinamine derivatives
NL1030863C2 (nl)	2006-12-28	Heteroaromatische chinolineverbindingen.
US5231184A (en)	1993-07-27	Pridazinamine derivatives
EP0156433B1 (en)	1991-02-27	Anti-virally active pyridazinamines
AU635100B2 (en)	1993-03-11	Antipicornaviral pyridazinamines
AU2005219525B2 (en)	2011-08-18	Fused derivatives of pyrazole
KR20250010152A (ko)	2025-01-20	Rna 헬리카제 dhx9의 억제제 및 이의 용도
AU2007240439A1 (en)	2007-11-01	Inhibitors of c-fms kinase
AU2011302216A1 (en)	2013-04-04	Phtalazine derivatives as JAK1 inhibitors
AU619111B2 (en)	1992-01-16	Antirhinoviral (thio) morpholinyl and piperazinyl alkylphenol ethers
KR19990028390A (ko)	1999-04-15	트리아졸 항진균제
US5106973A (en)	1992-04-21	Pyridzainamine derivatives
US5112825A (en)	1992-05-12	Antirhinoviral heteroamine-substituted pyridazines
EP0398427B1 (en)	1994-03-16	Antirhinoviral pyridazinamines
US5070090A (en)	1991-12-03	Antipicorpaviral herterocyclic-substituted morpholinyl alkylphenol ethers
US5196535A (en)	1993-03-23	Intermediates for producing antipicornaviral pyridazinamines
AU2013302859A1 (en)	2015-02-19	1,4-disubstituted pyridazine analogs and methods for treating SMN-deficiency-related conditions