PH27120A - Derivatives of 5-hydroxy and 5-methoxy 2-amino-pyridines as inhibitors of interleukin-1 production - Google Patents

Derivatives of 5-hydroxy and 5-methoxy 2-amino-pyridines as inhibitors of interleukin-1 production Download PDF

Info

Publication number: PH27120A
Authority: PH; Philippines
Prior art keywords: pharmaceutically; compound; interleukin; acceptable salt; mammal
Prior art date: 1988-12-14

Application number

PH39661A

Other languages

English (en)

Inventor

Frederick Judson Walker

Original Assignee

Pfizer

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.)

1988-12-14

Filing date

1989-12-11

Publication date

1993-03-16

1989-12-11 Application filed by Pfizer filed Critical Pfizer

1993-03-16 Publication of PH27120A publication Critical patent/PH27120A/en

Links

230000018276 interleukin-1 production Effects 0.000 title abstract description 10
239000003112 inhibitor Substances 0.000 title description 4
XJKJHILCYUUVSJ-UHFFFAOYSA-N 5-methoxypyridin-2-amine Chemical class COC1=CC=C(N)N=C1 XJKJHILCYUUVSJ-UHFFFAOYSA-N 0.000 title 1
238000000034 method Methods 0.000 claims abstract description 46
150000001875 compounds Chemical class 0.000 claims abstract description 44
150000003839 salts Chemical class 0.000 claims abstract description 32
241000124008 Mammalia Species 0.000 claims abstract description 21
102000000589 Interleukin-1 Human genes 0.000 claims abstract description 20
108010002352 Interleukin-1 Proteins 0.000 claims abstract description 20
230000001404 mediated effect Effects 0.000 claims abstract description 14
125000000217 alkyl group Chemical group 0.000 claims abstract description 10
210000002808 connective tissue Anatomy 0.000 claims abstract description 10
208000030159 metabolic disease Diseases 0.000 claims abstract description 9
125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 8
230000004064 dysfunction Effects 0.000 claims abstract description 6
208000026278 immune system disease Diseases 0.000 claims abstract description 6
125000003884 phenylalkyl group Chemical group 0.000 claims abstract description 5
208000018083 Bone metabolism disease Diseases 0.000 claims description 5
210000001519 tissue Anatomy 0.000 claims description 4
230000037390 scarring Effects 0.000 claims description 2
208000028169 periodontal disease Diseases 0.000 claims 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 7
210000000988 bone and bone Anatomy 0.000 abstract description 5
230000002401 inhibitory effect Effects 0.000 abstract description 5
125000001153 fluoro group Chemical group F* 0.000 abstract description 4
KAHHAPNRIQLSFT-UHFFFAOYSA-N 5-methoxypyrimidin-2-amine Chemical class COC1=CN=C(N)N=C1 KAHHAPNRIQLSFT-UHFFFAOYSA-N 0.000 abstract 1
210000004027 cell Anatomy 0.000 description 7
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
238000011282 treatment Methods 0.000 description 6
239000006146 Roswell Park Memorial Institute medium Substances 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
239000000243 solution Substances 0.000 description 5
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
201000004681 Psoriasis Diseases 0.000 description 4
239000003085 diluting agent Substances 0.000 description 4
208000035475 disorder Diseases 0.000 description 4
239000002609 medium Substances 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
206010028980 Neoplasm Diseases 0.000 description 3
208000008469 Peptic Ulcer Diseases 0.000 description 3
239000002253 acid Substances 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
201000011510 cancer Diseases 0.000 description 3
239000002552 dosage form Substances 0.000 description 3
239000002158 endotoxin Substances 0.000 description 3
239000000499 gel Substances 0.000 description 3
229920006008 lipopolysaccharide Polymers 0.000 description 3
239000000463 material Substances 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
208000006386 Bone Resorption Diseases 0.000 description 2
108091003079 Bovine Serum Albumin Proteins 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
208000024172 Cardiovascular disease Diseases 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
208000001132 Osteoporosis Diseases 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
208000026935 allergic disease Diseases 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
230000024279 bone resorption Effects 0.000 description 2
239000001569 carbon dioxide Substances 0.000 description 2
229910002092 carbon dioxide Inorganic materials 0.000 description 2
239000000969 carrier Substances 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
239000006071 cream Substances 0.000 description 2
230000001120 cytoprotective effect Effects 0.000 description 2
201000010099 disease Diseases 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000003995 emulsifying agent Substances 0.000 description 2
229960005293 etodolac Drugs 0.000 description 2
XFBVBWWRPKNWHW-UHFFFAOYSA-N etodolac Chemical compound C1COC(CC)(CC(O)=O)C2=N[C]3C(CC)=CC=CC3=C21 XFBVBWWRPKNWHW-UHFFFAOYSA-N 0.000 description 2
239000012091 fetal bovine serum Substances 0.000 description 2
ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 2
CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 2
230000002757 inflammatory effect Effects 0.000 description 2
150000002617 leukotrienes Chemical class 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000006210 lotion Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
239000000203 mixture Substances 0.000 description 2
239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 2
229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 2
239000002674 ointment Substances 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
238000007911 parenteral administration Methods 0.000 description 2
239000008194 pharmaceutical composition Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
230000002685 pulmonary effect Effects 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
239000008107 starch Substances 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
239000006228 supernatant Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
WOAHJDHKFWSLKE-UHFFFAOYSA-N 1,2-benzoquinone Chemical compound O=C1C=CC=CC1=O WOAHJDHKFWSLKE-UHFFFAOYSA-N 0.000 description 1
VCIHPVOAXJAJLZ-UHFFFAOYSA-N 2-amino-4-methylpyrimidin-5-ol Chemical compound CC1=NC(N)=NC=C1O VCIHPVOAXJAJLZ-UHFFFAOYSA-N 0.000 description 1
JIADELSANNMYFC-UHFFFAOYSA-N 5-methoxypyrimidine Chemical class COC1=CN=CN=C1 JIADELSANNMYFC-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
235000017060 Arachis glabrata Nutrition 0.000 description 1
244000105624 Arachis hypogaea Species 0.000 description 1
235000010777 Arachis hypogaea Nutrition 0.000 description 1
235000018262 Arachis monticola Nutrition 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
235000019739 Dicalciumphosphate Nutrition 0.000 description 1
238000002965 ELISA Methods 0.000 description 1
208000018522 Gastrointestinal disease Diseases 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
108010001336 Horseradish Peroxidase Proteins 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
206010020751 Hypersensitivity Diseases 0.000 description 1
206010021143 Hypoxia Diseases 0.000 description 1
HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical class 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 1
208000022559 Inflammatory bowel disease Diseases 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
240000007472 Leucaena leucocephala Species 0.000 description 1
235000010643 Leucaena leucocephala Nutrition 0.000 description 1
208000019693 Lung disease Diseases 0.000 description 1
240000003183 Manihot esculenta Species 0.000 description 1
235000016735 Manihot esculenta subsp esculenta Nutrition 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
229930182555 Penicillin Natural products 0.000 description 1
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
208000011191 Pulmonary vascular disease Diseases 0.000 description 1
241001222774 Salmonella enterica subsp. enterica serovar Minnesota Species 0.000 description 1
244000000231 Sesamum indicum Species 0.000 description 1
235000003434 Sesamum indicum Nutrition 0.000 description 1
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
244000061456 Solanum tuberosum Species 0.000 description 1
235000002595 Solanum tuberosum Nutrition 0.000 description 1
208000005392 Spasm Diseases 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
206010000891 acute myocardial infarction Diseases 0.000 description 1
239000000783 alginic acid Substances 0.000 description 1
235000010443 alginic acid Nutrition 0.000 description 1
229920000615 alginic acid Polymers 0.000 description 1
229960001126 alginic acid Drugs 0.000 description 1
150000004781 alginic acids Chemical class 0.000 description 1
230000000172 allergic effect Effects 0.000 description 1
230000007815 allergy Effects 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
206010003246 arthritis Diseases 0.000 description 1
239000010425 asbestos Substances 0.000 description 1
238000003556 assay Methods 0.000 description 1
208000006673 asthma Diseases 0.000 description 1
230000001363 autoimmune Effects 0.000 description 1
230000001580 bacterial effect Effects 0.000 description 1
235000019445 benzyl alcohol Nutrition 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000037396 body weight Effects 0.000 description 1
206010006451 bronchitis Diseases 0.000 description 1
-1 but not limited to Substances 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
239000006285 cell suspension Substances 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
238000004040 coloring Methods 0.000 description 1
239000003246 corticosteroid Substances 0.000 description 1
229960001334 corticosteroids Drugs 0.000 description 1
230000002939 deleterious effect Effects 0.000 description 1
NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
229940038472 dicalcium phosphate Drugs 0.000 description 1
229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000000975 dye Substances 0.000 description 1
230000002526 effect on cardiovascular system Effects 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
230000002708 enhancing effect Effects 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
239000012530 fluid Substances 0.000 description 1
230000004907 flux Effects 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000011521 glass Substances 0.000 description 1
239000008103 glucose Substances 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
230000007954 hypoxia Effects 0.000 description 1
229960001680 ibuprofen Drugs 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
238000011534 incubation Methods 0.000 description 1
229960000905 indomethacin Drugs 0.000 description 1
208000027866 inflammatory disease Diseases 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000010255 intramuscular injection Methods 0.000 description 1
239000007927 intramuscular injection Substances 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
230000007102 metabolic function Effects 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
239000011707 mineral Substances 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
230000008506 pathogenesis Effects 0.000 description 1
235000020232 peanut Nutrition 0.000 description 1
239000008188 pellet Substances 0.000 description 1
239000003961 penetration enhancing agent Substances 0.000 description 1
229940049954 penicillin Drugs 0.000 description 1
230000003239 periodontal effect Effects 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229910052573 porcelain Inorganic materials 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
208000002815 pulmonary hypertension Diseases 0.000 description 1
230000004044 response Effects 0.000 description 1
229910052895 riebeckite Inorganic materials 0.000 description 1
238000003118 sandwich ELISA Methods 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
241000894007 species Species 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000011550 stock solution Substances 0.000 description 1
229960005322 streptomycin Drugs 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000013268 sustained release Methods 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
230000000699 topical effect Effects 0.000 description 1

Classifications

- 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
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/02—Nutrients, e.g. vitamins, minerals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- 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

Landscapes

Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical & Material Sciences (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
General Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Epidemiology (AREA)
Nutrition Science (AREA)
Diabetes (AREA)
Hematology (AREA)
Obesity (AREA)
Immunology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Pyridine Compounds (AREA)
Saccharide Compounds (AREA)

PH39661A 1988-12-14 1989-12-11 Derivatives of 5-hydroxy and 5-methoxy 2-amino-pyridines as inhibitors of interleukin-1 production PH27120A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US28450588A	1988-12-14	1988-12-14

Publications (1)

Publication Number	Publication Date
PH27120A true PH27120A (en)	1993-03-16

Family

ID=23090453

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
PH39661A PH27120A (en)	1988-12-14	1989-12-11	Derivatives of 5-hydroxy and 5-methoxy 2-amino-pyridines as inhibitors of interleukin-1 production

Country Status (13)

Country	Link
EP (1)	EP0373827B1 (fr)
JP (1)	JPH0651622B2 (fr)
KR (1)	KR920003578B1 (fr)
AT (1)	ATE96321T1 (fr)
AU (1)	AU605702B2 (fr)
CA (1)	CA2005196A1 (fr)
DE (1)	DE68910288T2 (fr)
HU (1)	HU206182B (fr)
IE (1)	IE893978L (fr)
IL (1)	IL92586A (fr)
PH (1)	PH27120A (fr)
PT (1)	PT92551A (fr)
ZA (1)	ZA899508B (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5356898A (en) *	1991-01-31	1994-10-18	Warner-Lambert Company	Substituted 4,6-di-tertiary-butyl 5-hydroxy-pyrimidines
US5177079A (en) *	1991-01-31	1993-01-05	Warner-Lambert Company	2-substituted-4,6-di-tertiarybutyl-5-hydroxy-1,3-pyrimidines useful as antiinflammatory agents
US5248682A (en) *	1991-01-31	1993-09-28	Warner-Lambert Company	2-substituted-4,6-di-tertiary-butyl-5-hydroxy-1,3-pyrimidines useful as antiinflammatory agents
US5270319A (en) *	1991-09-09	1993-12-14	Warner-Lambert Company	5-hydroxy-2-pyrimidinylmethylene derivatives useful as antiinflammatory agents
DE102004054080A1 (de) *	2004-11-09	2006-05-11	Wella Ag	Haut- oder Haarbehandlungsmittel mit Schutzeffekt

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1670536B2 (de) *	1966-11-09	1975-05-28	Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler, 6000 Frankfurt	Neue 2-Anilino-5-acylamino-pyrimidlne
US4554276A (en) *	1983-10-03	1985-11-19	Pfizer Inc.	2-Amino-5-hydroxy-4-methylpyrimidine derivatives
IL77243A (en) *	1984-12-21	1996-11-14	Procter & Gamble	Pharmaceutical compositions containing geminal diphosphonic acid compounds and certain such novel compounds
US4711888A (en) *	1985-07-24	1987-12-08	Pfizer Inc.	Hydroxy and alkoxy pyrimidines

1989
- 1989-12-07 DE DE89312736T patent/DE68910288T2/de not_active Expired - Fee Related
- 1989-12-07 IL IL9258689A patent/IL92586A/en not_active IP Right Cessation
- 1989-12-07 AT AT89312736T patent/ATE96321T1/de not_active IP Right Cessation
- 1989-12-07 EP EP89312736A patent/EP0373827B1/fr not_active Expired - Lifetime
- 1989-12-11 PH PH39661A patent/PH27120A/en unknown
- 1989-12-11 JP JP1321232A patent/JPH0651622B2/ja not_active Expired - Lifetime
- 1989-12-12 AU AU46130/89A patent/AU605702B2/en not_active Ceased
- 1989-12-12 CA CA002005196A patent/CA2005196A1/fr not_active Abandoned
- 1989-12-12 PT PT92551A patent/PT92551A/pt not_active Application Discontinuation
- 1989-12-13 ZA ZA899508A patent/ZA899508B/xx unknown
- 1989-12-13 IE IE893978A patent/IE893978L/xx unknown
- 1989-12-13 KR KR1019890018435A patent/KR920003578B1/ko not_active Expired
- 1989-12-13 HU HU896526A patent/HU206182B/hu not_active IP Right Cessation

Also Published As

Publication number	Publication date
EP0373827B1 (fr)	1993-10-27
ZA899508B (en)	1991-07-31
ATE96321T1 (de)	1993-11-15
KR920003578B1 (ko)	1992-05-04
AU4613089A (en)	1990-07-19
CA2005196A1 (fr)	1990-06-14
HUT51897A (en)	1990-06-28
AU605702B2 (en)	1991-01-17
DE68910288T2 (de)	1994-02-17
JPH0651622B2 (ja)	1994-07-06
EP0373827A2 (fr)	1990-06-20
PT92551A (pt)	1990-06-29
IE893978L (en)	1990-06-14
JPH02218613A (ja)	1990-08-31
DE68910288D1 (de)	1993-12-02
HU206182B (en)	1992-09-28
IL92586A0 (en)	1990-08-31
EP0373827A3 (fr)	1991-11-06
KR900009078A (ko)	1990-07-02
IL92586A (en)	1994-06-24

Publication	Publication Date	Title
EP0739202B1 (fr)	1998-12-16	Utilisation de bis(amidinobenzimidazoles) dans la fabrication de medicaments destines a inhiber l'integrase retrovirale
US4861794A (en)	1989-08-29	3-substituted-2-oxindole-1-carboxamides as inhibitors of interleukin-1 biosynthesis
EP0373827B1 (fr)	1993-10-27	Dérivés de 5-hydroxy et 5-méthoxy-2-amino-pyrimidines comme inhibiteurs de la production d'interleukine-1
US5545656A (en)	1996-08-13	2-Oxidole-1-carboxamide pharmaceutical agents for the treatment of alzheimer's disease
US5071852A (en)	1991-12-10	Derivatives of 5-hydroxy and 5-methoxy 2-amino-pyrimidines as inhibitors of interleukin-1 production
EP0425109B1 (fr)	1994-08-03	Dérivés de 3-substitués-2-oxindole comme inhibiteurs de biosynthèse d'interleukine
WO1992003130A1 (fr)	1992-03-05	Utilisation de composes d'aryle hydroxyuree pour le traitement de l'atherosclerose
US5260328A (en)	1993-11-09	Phenyl-indenopurazol 3-oxo-propanamide derivatives useful in the treatment of rheumatoid arthritis
IE904432A1 (en)	1991-06-19	Inhibitors of pneumocystis carinii dihydrofolate reductase
NZ239215A (en)	1997-07-27	3-(benzothiazol-2-ylmethyl)-4-oxo-3h-phthalazin-1-ylacetic acid derivatives are used to make a blood uric acid level lowering medicament
US20080200557A1 (en)	2008-08-21	Method for Inhibiting Lipid Peroxidation
NZ235638A (en)	1997-02-24	The use of indole derivatives for treating interleukin-1 related disorders
JPS62158216A (ja)	1987-07-14	薬物の製造方法