SK5782001A3 - Benzoylpyridazine derivative, process for the preparation thereof and pharmaceutical composition containing same - Google Patents

Benzoylpyridazine derivative, process for the preparation thereof and pharmaceutical composition containing same Download PDF

Info

Publication number: SK5782001A3
Authority: SK; Slovakia
Prior art keywords: formula; physiologically acceptable; compound; group; acceptable salts
Prior art date: 1998-11-04

Application number

SK578-2001A

Other languages

English (en)

Slovak (sk)

Inventor

Rochus Jonas

Michael Wolf

Franz-Werner Kluxen

Original Assignee

Merck Patent Gmbh

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.)

1998-11-04

Filing date

1999-10-23

Publication date

2001-11-06

1999-10-23 Application filed by Merck Patent Gmbh filed Critical Merck Patent Gmbh

2001-11-06 Publication of SK5782001A3 publication Critical patent/SK5782001A3/sk

Links

VDWSVBMVZLRATD-UHFFFAOYSA-N phenyl(pyridazin-3-yl)methanone Chemical class C=1C=CN=NC=1C(=O)C1=CC=CC=C1 VDWSVBMVZLRATD-UHFFFAOYSA-N 0.000 title claims abstract description 7
238000000034 method Methods 0.000 title claims description 10
239000008194 pharmaceutical composition Substances 0.000 title claims description 7
238000002360 preparation method Methods 0.000 title claims description 6
208000006673 asthma Diseases 0.000 claims abstract description 10
206010028980 Neoplasm Diseases 0.000 claims abstract description 6
206010012601 diabetes mellitus Diseases 0.000 claims abstract description 5
201000006417 multiple sclerosis Diseases 0.000 claims abstract description 5
206010039073 rheumatoid arthritis Diseases 0.000 claims abstract description 5
208000030507 AIDS Diseases 0.000 claims abstract description 4
201000001320 Atherosclerosis Diseases 0.000 claims abstract description 4
208000023275 Autoimmune disease Diseases 0.000 claims abstract description 4
206010006895 Cachexia Diseases 0.000 claims abstract description 4
208000001132 Osteoporosis Diseases 0.000 claims abstract description 4
230000004054 inflammatory process Effects 0.000 claims abstract description 4
206010020751 Hypersensitivity Diseases 0.000 claims abstract description 3
230000007815 allergy Effects 0.000 claims abstract description 3
150000001875 compounds Chemical class 0.000 claims description 66
-1 3-dimethylaminopropyl {4- [3- (3-ethoxy-4-methoxyphenyl) 1,2,3,4-tetrahydropyridazin-1-ylcarbonyl] phenyl} carbamate Chemical class 0.000 claims description 44
150000003839 salts Chemical class 0.000 claims description 26
238000006243 chemical reaction Methods 0.000 claims description 14
125000004432 carbon atom Chemical group C* 0.000 claims description 11
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
239000004480 active ingredient Substances 0.000 claims description 9
229910052801 chlorine Inorganic materials 0.000 claims description 9
239000012453 solvate Substances 0.000 claims description 9
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
229910052794 bromium Inorganic materials 0.000 claims description 8
239000000460 chlorine Substances 0.000 claims description 8
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
239000002253 acid Substances 0.000 claims description 7
229910052731 fluorine Inorganic materials 0.000 claims description 7
239000011737 fluorine Substances 0.000 claims description 7
238000004519 manufacturing process Methods 0.000 claims description 7
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
229910052740 iodine Inorganic materials 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 5
125000002947 alkylene group Chemical group 0.000 claims description 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
201000010099 disease Diseases 0.000 claims description 4
125000000623 heterocyclic group Chemical group 0.000 claims description 4
239000007788 liquid Substances 0.000 claims description 4
206010009900 Colitis ulcerative Diseases 0.000 claims description 3
206010061218 Inflammation Diseases 0.000 claims description 3
206010052779 Transplant rejections Diseases 0.000 claims description 3
201000006704 Ulcerative Colitis Diseases 0.000 claims description 3
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
239000011630 iodine Substances 0.000 claims description 3
229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
239000002552 dosage form Substances 0.000 claims description 2
229910052757 nitrogen Inorganic materials 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
239000000546 pharmaceutical excipient Substances 0.000 claims description 2
239000002587 phosphodiesterase IV inhibitor Substances 0.000 claims description 2
239000007787 solid Substances 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
125000004434 sulfur atom Chemical group 0.000 claims description 2
125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 1
HFZPZJPGUCSPPT-UHFFFAOYSA-N CCOC1=C(C=CC(=C1)C2CC=CN(N2)C(=O)C3=CC=C(C=C3)OC(=O)N)OC Chemical compound CCOC1=C(C=CC(=C1)C2CC=CN(N2)C(=O)C3=CC=C(C=C3)OC(=O)N)OC HFZPZJPGUCSPPT-UHFFFAOYSA-N 0.000 claims 1
150000007514 bases Chemical class 0.000 claims 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
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108010037584 Type 4 Cyclic Nucleotide Phosphodiesterases Proteins 0.000 abstract description 2
230000002401 inhibitory effect Effects 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
239000000243 solution Substances 0.000 description 9
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LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
239000003814 drug Substances 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
239000007858 starting material Substances 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
239000003826 tablet Substances 0.000 description 5
DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 5
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
125000000719 pyrrolidinyl group Chemical group 0.000 description 4
IURTZMKFDMHXRF-UHFFFAOYSA-N 3-(dimethylamino)propyl carbonochloridate Chemical compound CN(C)CCCOC(Cl)=O IURTZMKFDMHXRF-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
206010012438 Dermatitis atopic Diseases 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
201000008937 atopic dermatitis Diseases 0.000 description 3
239000002585 base Substances 0.000 description 3
210000000988 bone and bone Anatomy 0.000 description 3
239000002775 capsule Substances 0.000 description 3
239000012154 double-distilled water Substances 0.000 description 3
239000012442 inert solvent Substances 0.000 description 3
230000005764 inhibitory process Effects 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
125000003386 piperidinyl group Chemical group 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
239000000454 talc Substances 0.000 description 3
235000012222 talc Nutrition 0.000 description 3
229910052623 talc Inorganic materials 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
125000004791 2-fluoroethoxy group Chemical group FCCO* 0.000 description 2
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
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 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
201000004681 Psoriasis Diseases 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
108060008682 Tumor Necrosis Factor Proteins 0.000 description 2
239000013543 active substance Substances 0.000 description 2
208000026935 allergic disease Diseases 0.000 description 2
230000037396 body weight Effects 0.000 description 2
MKZRYHJQHATKLV-UHFFFAOYSA-N diazinan-1-yl(phenyl)methanone Chemical class C=1C=CC=CC=1C(=O)N1CCCCN1 MKZRYHJQHATKLV-UHFFFAOYSA-N 0.000 description 2
BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 2
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125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
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238000010265 fast atom bombardment Methods 0.000 description 2
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239000007924 injection Substances 0.000 description 2
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SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
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235000019359 magnesium stearate Nutrition 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
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239000007921 spray Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
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125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 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 description 2
URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 2
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FKTCBHHHFUUZDI-UHFFFAOYSA-N (1-methylpiperidin-4-yl) carbonochloridate Chemical compound CN1CCC(OC(Cl)=O)CC1 FKTCBHHHFUUZDI-UHFFFAOYSA-N 0.000 description 1
AHAKTZWVAMQISB-UHFFFAOYSA-N (4-aminophenyl)-[6-(3-ethoxy-4-methoxyphenyl)-5,6-dihydro-1h-pyridazin-2-yl]methanone Chemical compound C1=C(OC)C(OCC)=CC(C2NN(C=CC2)C(=O)C=2C=CC(N)=CC=2)=C1 AHAKTZWVAMQISB-UHFFFAOYSA-N 0.000 description 1
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WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
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OOSZCNKVJAVHJI-UHFFFAOYSA-N 1-[(4-fluorophenyl)methyl]piperazine Chemical compound C1=CC(F)=CC=C1CN1CCNCC1 OOSZCNKVJAVHJI-UHFFFAOYSA-N 0.000 description 1
125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
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KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical group CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
125000006023 1-pentenyl group Chemical group 0.000 description 1
125000006017 1-propenyl group Chemical group 0.000 description 1
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125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
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 1
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206010006451 bronchitis Diseases 0.000 description 1
239000000872 buffer Substances 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
XNRHTMDHGDWBGP-UHFFFAOYSA-N carbamic acid;hydrochloride Chemical compound Cl.NC(O)=O XNRHTMDHGDWBGP-UHFFFAOYSA-N 0.000 description 1
235000014633 carbohydrates Nutrition 0.000 description 1
150000001720 carbohydrates Chemical class 0.000 description 1
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150000001735 carboxylic acids Chemical class 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
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208000007451 chronic bronchitis Diseases 0.000 description 1
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238000000576 coating method Methods 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
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239000003086 colorant Substances 0.000 description 1
239000006071 cream Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
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
230000000593 degrading effect Effects 0.000 description 1
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
229910000397 disodium phosphate Inorganic materials 0.000 description 1
235000019800 disodium phosphate Nutrition 0.000 description 1
MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
239000006196 drop Substances 0.000 description 1
239000000890 drug combination Substances 0.000 description 1
239000000975 dye Substances 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
239000003889 eye drop Substances 0.000 description 1
229940012356 eye drops Drugs 0.000 description 1
239000012467 final product Substances 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
239000012458 free base Substances 0.000 description 1
235000011389 fruit/vegetable juice Nutrition 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
235000013773 glyceryl triacetate Nutrition 0.000 description 1
239000008187 granular material Substances 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
239000007943 implant Substances 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
230000003834 intracellular effect Effects 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000003446 ligand Substances 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
230000009401 metastasis Effects 0.000 description 1
239000011707 mineral Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
YZMHQCWXYHARLS-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C21 YZMHQCWXYHARLS-UHFFFAOYSA-N 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
150000002828 nitro derivatives Chemical class 0.000 description 1
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
229940066842 petrolatum Drugs 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical class OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
239000006187 pill Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
102000003998 progesterone receptors Human genes 0.000 description 1
108090000468 progesterone receptors Proteins 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
208000017520 skin disease Diseases 0.000 description 1
229940074545 sodium dihydrogen phosphate dihydrate Drugs 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000008347 soybean phospholipid Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000007940 sugar coated tablet Substances 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
229960002622 triacetin Drugs 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
230000004614 tumor growth Effects 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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239000011782 vitamin Substances 0.000 description 1
229940088594 vitamin Drugs 0.000 description 1
229930003231 vitamin Natural products 0.000 description 1
235000013343 vitamin Nutrition 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- 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
- C07D237/04—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having less than three double bonds between ring members or between ring members and non-ring members
- 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
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- 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
- A61P11/06—Antiasthmatics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
- 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
- A61P31/18—Antivirals for RNA viruses for HIV
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- 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
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
- 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
- A61P37/08—Antiallergic agents
- 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
- 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
- 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

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Immunology (AREA)
Physical Education & Sports Medicine (AREA)
Rheumatology (AREA)
Orthopedic Medicine & Surgery (AREA)
Pulmonology (AREA)
Diabetes (AREA)
Virology (AREA)
Cardiology (AREA)
Pain & Pain Management (AREA)
Heart & Thoracic Surgery (AREA)
Emergency Medicine (AREA)
Endocrinology (AREA)
Hematology (AREA)
Obesity (AREA)
AIDS & HIV (AREA)
Tropical Medicine & Parasitology (AREA)
Molecular Biology (AREA)
Vascular Medicine (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Urology & Nephrology (AREA)
Transplantation (AREA)

SK578-2001A 1998-11-04 1999-10-23 Benzoylpyridazine derivative, process for the preparation thereof and pharmaceutical composition containing same SK5782001A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19850701A DE19850701A1 (de)	1998-11-04	1998-11-04	Benzoylpyridazine
PCT/EP1999/008047 WO2000026201A1 (de)	1998-11-04	1999-10-23	Benzoylpyridazine

Publications (1)

Publication Number	Publication Date
SK5782001A3 true SK5782001A3 (en)	2001-11-06

Family

ID=7886577

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK578-2001A SK5782001A3 (en)	1998-11-04	1999-10-23	Benzoylpyridazine derivative, process for the preparation thereof and pharmaceutical composition containing same

Country Status (24)

Country	Link
US (1)	US6376493B1 (da)
EP (1)	EP1124809B1 (da)
JP (1)	JP4354652B2 (da)
KR (1)	KR20010075636A (da)
CN (1)	CN1142153C (da)
AR (1)	AR021068A1 (da)
AT (1)	ATE262513T1 (da)
AU (1)	AU759328B2 (da)
BR (1)	BR9915004A (da)
CA (1)	CA2349232A1 (da)
CZ (1)	CZ20011551A3 (da)
DE (2)	DE19850701A1 (da)
DK (1)	DK1124809T3 (da)
ES (1)	ES2214891T3 (da)
HU (1)	HUP0104033A3 (da)
ID (1)	ID28816A (da)
NO (1)	NO20012188D0 (da)
PL (1)	PL346909A1 (da)
PT (1)	PT1124809E (da)
SI (1)	SI1124809T1 (da)
SK (1)	SK5782001A3 (da)
TW (1)	TW458970B (da)
WO (1)	WO2000026201A1 (da)
ZA (1)	ZA200104541B (da)

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE19915364A1 (de) *	1999-04-06	2000-10-12	Merck Patent Gmbh	Verwendung von Arylalkanoylpyridazinen
DE10064997A1 (de) *	2000-12-23	2002-06-27	Merck Patent Gmbh	Benzoylpyridazine
US20050070529A1 (en) *	2001-02-12	2005-03-31	Merk Pantent Gmbh	Use of type 4 phosphodiesterase inhibitors in myocardial diseases
HUP0401747A3 (en)	2001-11-05	2005-06-28	Merck Patent Gmbh	Piridazine derivatives of hydrazono-malonitriles, their use, process for preparation of the compounds and pharmaceutical compositions containing the compounds
KR100866286B1 (ko) *	2001-11-29	2008-10-31	씨제이제일제당 (주)	신규한 카테콜 히드라지드 유도체 및 그의 제조방법
KR100508156B1 (ko) *	2002-11-29	2005-08-17	씨제이 주식회사	신규한 캐테콜 히드라자이드 유도체
EP1928437A2 (en)	2005-08-26	2008-06-11	Braincells, Inc.	Neurogenesis by muscarinic receptor modulation
EP2258358A3 (en)	2005-08-26	2011-09-07	Braincells, Inc.	Neurogenesis with acetylcholinesterase inhibitor
EP1940389A2 (en)	2005-10-21	2008-07-09	Braincells, Inc.	Modulation of neurogenesis by pde inhibition
US20070112017A1 (en)	2005-10-31	2007-05-17	Braincells, Inc.	Gaba receptor mediated modulation of neurogenesis
US20100216734A1 (en)	2006-03-08	2010-08-26	Braincells, Inc.	Modulation of neurogenesis by nootropic agents
AU2007249399A1 (en)	2006-05-09	2007-11-22	Braincells, Inc.	Neurogenesis by modulating angiotensin
US20100184806A1 (en)	2006-09-19	2010-07-22	Braincells, Inc.	Modulation of neurogenesis by ppar agents
WO2010099217A1 (en)	2009-02-25	2010-09-02	Braincells, Inc.	Modulation of neurogenesis using d-cycloserine combinations
WO2013106547A1 (en)	2012-01-10	2013-07-18	President And Fellows Of Harvard College	Beta-cell replication promoting compounds and methods of their use
CN113264899B (zh) *	2021-04-09	2022-06-14	台州学院	一种1，3，5-噁二嗪类化合物及其制备和应用

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DK0650480T3 (da)	1992-07-01	2002-05-13	Ortho Pharma Corp	1-Arylsulfonyl-3-phenyl-1,4,5,6-tetrahydropyridaziner
DE19514568A1 (de)	1995-04-20	1996-10-24	Merck Patent Gmbh	Arylalkyl-pyridazinone
DE19632549A1 (de) *	1996-08-13	1998-02-19	Merck Patent Gmbh	Arylalkanoylpyridazine

1998
- 1998-11-04 DE DE19850701A patent/DE19850701A1/de not_active Withdrawn
1999
- 1999-10-23 AU AU63423/99A patent/AU759328B2/en not_active Ceased
- 1999-10-23 ES ES99950775T patent/ES2214891T3/es not_active Expired - Lifetime
- 1999-10-23 KR KR1020017004759A patent/KR20010075636A/ko not_active Ceased
- 1999-10-23 SI SI9930542T patent/SI1124809T1/xx unknown
- 1999-10-23 WO PCT/EP1999/008047 patent/WO2000026201A1/de not_active Ceased
- 1999-10-23 PL PL99346909A patent/PL346909A1/xx unknown
- 1999-10-23 EP EP99950775A patent/EP1124809B1/de not_active Expired - Lifetime
- 1999-10-23 SK SK578-2001A patent/SK5782001A3/sk unknown
- 1999-10-23 BR BR9915004-2A patent/BR9915004A/pt not_active IP Right Cessation
- 1999-10-23 JP JP2000579590A patent/JP4354652B2/ja not_active Expired - Fee Related
- 1999-10-23 CN CNB998127469A patent/CN1142153C/zh not_active Expired - Fee Related
- 1999-10-23 ID IDW00200101082A patent/ID28816A/id unknown
- 1999-10-23 DK DK99950775T patent/DK1124809T3/da active
- 1999-10-23 CZ CZ20011551A patent/CZ20011551A3/cs unknown
- 1999-10-23 AT AT99950775T patent/ATE262513T1/de not_active IP Right Cessation
- 1999-10-23 US US09/830,957 patent/US6376493B1/en not_active Expired - Fee Related
- 1999-10-23 PT PT99950775T patent/PT1124809E/pt unknown
- 1999-10-23 HU HU0104033A patent/HUP0104033A3/hu unknown
- 1999-10-23 DE DE59908968T patent/DE59908968D1/de not_active Expired - Lifetime
- 1999-10-23 CA CA002349232A patent/CA2349232A1/en not_active Abandoned
- 1999-10-29 TW TW088118837A patent/TW458970B/zh not_active IP Right Cessation
- 1999-11-03 AR ARP990105552A patent/AR021068A1/es not_active Application Discontinuation
2001
- 2001-05-03 NO NO20012188A patent/NO20012188D0/no not_active Application Discontinuation
- 2001-06-01 ZA ZA200104541A patent/ZA200104541B/en unknown

Also Published As

Publication number	Publication date
HUP0104033A3 (en)	2002-08-28
US6376493B1 (en)	2002-04-23
NO20012188L (no)	2001-05-03
ID28816A (id)	2001-07-05
EP1124809B1 (de)	2004-03-24
DE59908968D1 (de)	2004-04-29
CN1324350A (zh)	2001-11-28
AR021068A1 (es)	2002-06-12
NO20012188D0 (no)	2001-05-03
AU759328B2 (en)	2003-04-10
CA2349232A1 (en)	2000-05-11
EP1124809A1 (de)	2001-08-22
CN1142153C (zh)	2004-03-17
JP2002528536A (ja)	2002-09-03
HUP0104033A2 (hu)	2002-05-29
ZA200104541B (en)	2002-09-02
TW458970B (en)	2001-10-11
JP4354652B2 (ja)	2009-10-28
DK1124809T3 (da)	2004-07-19
ES2214891T3 (es)	2004-09-16
CZ20011551A3 (cs)	2001-08-15
SI1124809T1 (en)	2004-06-30
ATE262513T1 (de)	2004-04-15
PT1124809E (pt)	2004-07-30
PL346909A1 (en)	2002-03-11
AU6342399A (en)	2000-05-22
BR9915004A (pt)	2001-11-13
DE19850701A1 (de)	2000-05-11
WO2000026201A1 (de)	2000-05-11
KR20010075636A (ko)	2001-08-09

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