IL125072A - HISTORY OF PYRIDO - 4,2,1 thiodiazine-3 amine and pharmaceutical preparations containing them - Google Patents

HISTORY OF PYRIDO - 4,2,1 thiodiazine-3 amine and pharmaceutical preparations containing them

Info

Publication number: IL125072A
Authority: IL; Israel
Prior art keywords: alkyl; alkoxy; cycloalkyl; halogen; hydroxy
Prior art date: 1996-01-17

Application number

IL12507297A

Other languages

English (en)

Hebrew (he)

Other versions

IL125072A0 (en

Original Assignee

Novo Nordisk As

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.)

1996-01-17

Filing date

1997-01-16

Publication date

2002-12-01

1997-01-16 Application filed by Novo Nordisk As filed Critical Novo Nordisk As

1999-01-26 Publication of IL125072A0 publication Critical patent/IL125072A0/xx

2002-12-01 Publication of IL125072A publication Critical patent/IL125072A/en

Links

239000008194 pharmaceutical composition Substances 0.000 title claims description 9
VOOIJSIVWKQHCW-UHFFFAOYSA-N 2H-pyrido[2,3-e][1,2,4]thiadiazin-3-amine Chemical class S1NC(=NC2=C1C=CC=N2)N VOOIJSIVWKQHCW-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 131
239000000203 mixture Substances 0.000 claims abstract description 25
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 14
201000010099 disease Diseases 0.000 claims abstract description 13
-1 C1-6 -alkoxy Chemical group 0.000 claims description 148
229910052736 halogen Inorganic materials 0.000 claims description 76
150000002367 halogens Chemical group 0.000 claims description 74
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 71
229910052739 hydrogen Inorganic materials 0.000 claims description 68
239000001257 hydrogen Substances 0.000 claims description 68
125000003118 aryl group Chemical group 0.000 claims description 51
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 44
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 34
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 30
125000004093 cyano group Chemical group *C#N 0.000 claims description 22
125000004432 carbon atom Chemical group C* 0.000 claims description 20
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 19
125000002252 acyl group Chemical group 0.000 claims description 19
125000004104 aryloxy group Chemical group 0.000 claims description 18
125000004663 dialkyl amino group Chemical group 0.000 claims description 18
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 17
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 17
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical compound [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 17
150000003839 salts Chemical class 0.000 claims description 17
229910052717 sulfur Inorganic materials 0.000 claims description 16
125000004122 cyclic group Chemical group 0.000 claims description 14
125000004433 nitrogen atom Chemical group N* 0.000 claims description 13
229910052760 oxygen Inorganic materials 0.000 claims description 13
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
239000001301 oxygen Substances 0.000 claims description 11
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
125000004434 sulfur atom Chemical group 0.000 claims description 11
125000002102 aryl alkyloxo group Chemical group 0.000 claims description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
125000001072 heteroaryl group Chemical group 0.000 claims description 9
229910052757 nitrogen Inorganic materials 0.000 claims description 9
125000004043 oxo group Chemical group O=* 0.000 claims description 9
239000011593 sulfur Substances 0.000 claims description 9
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 8
102000004257 Potassium Channel Human genes 0.000 claims description 8
239000002253 acid Substances 0.000 claims description 8
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 8
125000005135 aryl sulfinyl group Chemical group 0.000 claims description 8
125000005110 aryl thio group Chemical group 0.000 claims description 8
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
125000001715 oxadiazolyl group Chemical group 0.000 claims description 8
108020001213 potassium channel Proteins 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 8
125000004391 aryl sulfonyl group Chemical group 0.000 claims description 7
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 7
125000004430 oxygen atom Chemical group O* 0.000 claims description 7
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 6
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
125000003710 aryl alkyl group Chemical group 0.000 claims description 6
125000002950 monocyclic group Chemical group 0.000 claims description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
239000003085 diluting agent Substances 0.000 claims description 5
230000003287 optical effect Effects 0.000 claims description 5
150000001602 bicycloalkyls Chemical group 0.000 claims description 4
125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 4
125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 4
125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims description 4
125000004671 dialkylaminothiocarbonyl group Chemical group 0.000 claims description 4
239000003814 drug Substances 0.000 claims description 3
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
125000004446 heteroarylalkyl group Chemical group 0.000 claims description 3
MLOXGOOXOAHHIO-UHFFFAOYSA-N n-benzyl-1,1-dioxo-4h-pyrido[2,3-e][1,2,4]thiadiazin-3-amine Chemical compound N1C2=NC=CC=C2S(=O)(=O)N=C1NCC1=CC=CC=C1 MLOXGOOXOAHHIO-UHFFFAOYSA-N 0.000 claims description 3
OSELHUYSTVPUMM-UHFFFAOYSA-N n-benzyl-1,1-dioxo-4h-pyrido[4,3-e][1,2,4]thiadiazin-3-amine Chemical compound N1C2=CC=NC=C2S(=O)(=O)N=C1NCC1=CC=CC=C1 OSELHUYSTVPUMM-UHFFFAOYSA-N 0.000 claims description 3
YJYZILBQHNTWCL-UHFFFAOYSA-N n-benzyl-7-chloro-1,1-dioxo-4h-pyrido[2,3-e][1,2,4]thiadiazin-3-amine Chemical compound N=1S(=O)(=O)C2=CC(Cl)=CN=C2NC=1NCC1=CC=CC=C1 YJYZILBQHNTWCL-UHFFFAOYSA-N 0.000 claims description 3
125000004076 pyridyl group Chemical group 0.000 claims description 3
230000001105 regulatory effect Effects 0.000 claims description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
OCVOTQDPONHTMY-UHFFFAOYSA-N n-(1-methoxypropan-2-yl)-1,1-dioxo-4h-pyrido[4,3-e][1,2,4]thiadiazin-3-amine Chemical compound N1=CC=C2NC(NC(C)COC)=NS(=O)(=O)C2=C1 OCVOTQDPONHTMY-UHFFFAOYSA-N 0.000 claims description 2
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 2
150000002431 hydrogen Chemical group 0.000 claims 9
125000002619 bicyclic group Chemical group 0.000 claims 4
239000003937 drug carrier Substances 0.000 claims 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims 2
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 1
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims 1
UZCJQHJNSLRUTB-UHFFFAOYSA-N n-benzyl-2-methyl-1,1-dioxopyrido[4,3-e][1,2,4]thiadiazin-3-amine Chemical compound N=1C2=CC=NC=C2S(=O)(=O)N(C)C=1NCC1=CC=CC=C1 UZCJQHJNSLRUTB-UHFFFAOYSA-N 0.000 claims 1
238000000034 method Methods 0.000 abstract description 24
210000003169 central nervous system Anatomy 0.000 abstract description 7
IJVLTOQSGLWUMT-UHFFFAOYSA-N 2h-pyrido[2,3-e][1,2,4]thiadiazine Chemical compound C1=CN=C2NC=NSC2=C1 IJVLTOQSGLWUMT-UHFFFAOYSA-N 0.000 abstract description 3
210000000748 cardiovascular system Anatomy 0.000 abstract description 3
210000005095 gastrointestinal system Anatomy 0.000 abstract description 3
230000002685 pulmonary effect Effects 0.000 abstract description 3
PTITYRPDHMISBW-UHFFFAOYSA-N 2h-pyrido[3,2-b][1,4]thiazine Chemical class C1=CN=C2N=CCSC2=C1 PTITYRPDHMISBW-UHFFFAOYSA-N 0.000 abstract description 2
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
238000001914 filtration Methods 0.000 description 15
125000001424 substituent group Chemical group 0.000 description 15
239000002244 precipitate Substances 0.000 description 14
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
229940127315 Potassium Channel Openers Drugs 0.000 description 12
NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 12
239000000706 filtrate Substances 0.000 description 11
125000004429 atom Chemical group 0.000 description 10
239000003610 charcoal Substances 0.000 description 10
229940106265 charcoal Drugs 0.000 description 10
125000004169 (C1-C6) alkyl group Chemical group 0.000 description 9
239000000243 solution Substances 0.000 description 9
206010012601 diabetes mellitus Diseases 0.000 description 8
239000002904 solvent Substances 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 7
238000004821 distillation Methods 0.000 description 7
230000003914 insulin secretion Effects 0.000 description 7
102000004877 Insulin Human genes 0.000 description 6
108090001061 Insulin Proteins 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
150000001412 amines Chemical class 0.000 description 6
229940125396 insulin Drugs 0.000 description 6
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 5
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 5
206010060378 Hyperinsulinaemia Diseases 0.000 description 5
241001465754 Metazoa Species 0.000 description 5
125000003277 amino group Chemical group 0.000 description 5
210000004027 cell Anatomy 0.000 description 5
239000008103 glucose Substances 0.000 description 5
150000002430 hydrocarbons Chemical group 0.000 description 5
239000002609 medium Substances 0.000 description 5
150000004682 monohydrates Chemical class 0.000 description 5
239000000725 suspension Substances 0.000 description 5
VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 4
210000002237 B-cell of pancreatic islet Anatomy 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
239000002775 capsule Substances 0.000 description 4
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
238000001816 cooling Methods 0.000 description 4
GDLBFKVLRPITMI-UHFFFAOYSA-N diazoxide Chemical compound ClC1=CC=C2NC(C)=NS(=O)(=O)C2=C1 GDLBFKVLRPITMI-UHFFFAOYSA-N 0.000 description 4
230000000694 effects Effects 0.000 description 4
230000002124 endocrine Effects 0.000 description 4
230000035879 hyperinsulinaemia Effects 0.000 description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
229930195734 saturated hydrocarbon Natural products 0.000 description 4
210000002460 smooth muscle Anatomy 0.000 description 4
239000000126 substance Substances 0.000 description 4
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 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
ZKHQWZAMYRWXGA-UHFFFAOYSA-N Adenosine triphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)C(O)C1O ZKHQWZAMYRWXGA-UHFFFAOYSA-N 0.000 description 3
201000006474 Brain Ischemia Diseases 0.000 description 3
206010008120 Cerebral ischaemia Diseases 0.000 description 3
108091006146 Channels Proteins 0.000 description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
241000700159 Rattus Species 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
239000000872 buffer Substances 0.000 description 3
206010008118 cerebral infarction Diseases 0.000 description 3
125000000753 cycloalkyl group Chemical group 0.000 description 3
229960004042 diazoxide Drugs 0.000 description 3
229960004132 diethyl ether Drugs 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
235000019253 formic acid Nutrition 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
238000011534 incubation Methods 0.000 description 3
239000002198 insoluble material Substances 0.000 description 3
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 3
230000000144 pharmacologic effect Effects 0.000 description 3
230000002265 prevention Effects 0.000 description 3
239000007787 solid Substances 0.000 description 3
238000012360 testing method Methods 0.000 description 3
208000001072 type 2 diabetes mellitus Diseases 0.000 description 3
210000003932 urinary bladder Anatomy 0.000 description 3
ACBJUYCGPOQJND-UHFFFAOYSA-N 1,1-dioxo-4h-pyrido[4,3-e][1,2,4]thiadiazin-3-amine Chemical compound N1=CC=C2NC(N)=NS(=O)(=O)C2=C1 ACBJUYCGPOQJND-UHFFFAOYSA-N 0.000 description 2
125000001766 1,2,4-oxadiazol-3-yl group Chemical group [H]C1=NC(*)=NO1 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 2
125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
XOAKQCOPHMCADA-UHFFFAOYSA-N 4,8-dioxatricyclo[5.1.0.03,5]octane Chemical compound C1C2OC2CC2OC12 XOAKQCOPHMCADA-UHFFFAOYSA-N 0.000 description 2
QHZHTIBIPAZLDQ-UHFFFAOYSA-N 7-chloro-n-hexyl-1,1-dioxo-4h-pyrido[2,3-e][1,2,4]thiadiazin-3-amine Chemical compound ClC1=CN=C2NC(NCCCCCC)=NS(=O)(=O)C2=C1 QHZHTIBIPAZLDQ-UHFFFAOYSA-N 0.000 description 2
KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
201000004384 Alopecia Diseases 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
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SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical group C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
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208000006399 Premature Obstetric Labor Diseases 0.000 description 2
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KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical group C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical group N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
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229940125898 compound 5 Drugs 0.000 description 2
239000013078 crystal Substances 0.000 description 2
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
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 2
125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 2
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 2
238000010908 decantation Methods 0.000 description 2
RAFNCPHFRHZCPS-UHFFFAOYSA-N di(imidazol-1-yl)methanethione Chemical compound C1=CN=CN1C(=S)N1C=CN=C1 RAFNCPHFRHZCPS-UHFFFAOYSA-N 0.000 description 2
235000014113 dietary fatty acids Nutrition 0.000 description 2
239000008298 dragée Substances 0.000 description 2
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125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
229930195729 fatty acid Natural products 0.000 description 2
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Classifications

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- 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
- A61P5/00—Drugs for disorders of the endocrine system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/48—Drugs for disorders of the endocrine system of the pancreatic hormones
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/48—Drugs for disorders of the endocrine system of the pancreatic hormones
- A61P5/50—Drugs for disorders of the endocrine system of the pancreatic hormones for increasing or potentiating the activity of insulin
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
- 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

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Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Public Health (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Veterinary Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Diabetes (AREA)
Endocrinology (AREA)
Biomedical Technology (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Heart & Thoracic Surgery (AREA)
Pulmonology (AREA)
Urology & Nephrology (AREA)
Cardiology (AREA)
Obesity (AREA)
Hematology (AREA)
Dermatology (AREA)
Pain & Pain Management (AREA)
Emergency Medicine (AREA)
Vascular Medicine (AREA)
Hospice & Palliative Care (AREA)
Psychiatry (AREA)
Reproductive Health (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Steroid Compounds (AREA)

IL12507297A 1996-01-17 1997-01-16 HISTORY OF PYRIDO - 4,2,1 thiodiazine-3 amine and pharmaceutical preparations containing them IL125072A (en)

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
DK4296		1996-01-17
DK24796		1996-03-05
DK24696		1996-03-05
DK24996		1996-03-05
DK24896		1996-03-05
PCT/DK1997/000018 WO1997026264A1 (en)	1996-01-17	1997-01-16	Pyrido-1,2,4-thiadiazine and pyrido-1,4-thiazine derivatives, their preparation and use

Publications (2)

Publication Number	Publication Date
IL125072A0 IL125072A0 (en)	1999-01-26
IL125072A true IL125072A (en)	2002-12-01

Family

ID=27512741

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL12507297A IL125072A (en)	1996-01-17	1997-01-16	HISTORY OF PYRIDO - 4,2,1 thiodiazine-3 amine and pharmaceutical preparations containing them

Country Status (16)

Country	Link
US (1)	US5792764A (de)
EP (1)	EP0877748B1 (de)
JP (1)	JP2000503651A (de)
KR (1)	KR19990077320A (de)
CN (1)	CN1208418A (de)
AT (1)	ATE281460T1 (de)
AU (1)	AU727905B2 (de)
BR (1)	BR9707004A (de)
CA (1)	CA2241565A1 (de)
CZ (1)	CZ220598A3 (de)
DE (1)	DE69731458T2 (de)
IL (1)	IL125072A (de)
NO (1)	NO983285L (de)
PL (1)	PL327927A1 (de)
RU (1)	RU2193564C2 (de)
WO (1)	WO1997026264A1 (de)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6329368B1 (en) *	1997-05-09	2001-12-11	The Regents Of The University Of California	Endocrine modulation with positive modulators of AMPA type glutamate receptors
WO1999032495A1 (en) *	1997-12-19	1999-07-01	Novo Nordisk A/S	Pyrido 1,2,4-thiadiazine derivatives, their preparation and use
WO2002000222A1 (en) *	2000-06-26	2002-01-03	Novo Nordisk A/S	Use of potassium channel agonists for the treatment of cancer
WO2003045955A1 (en) *	2001-11-30	2003-06-05	Novo Nordisk A/S	Use of selective potassium channel openers
AU2002342600A1 (en) *	2001-11-30	2003-06-10	Novo Nordisk A/S	Use of selective potassium channel openers
US20030109519A1 (en) *	2001-11-30	2003-06-12	Jeppe Sturis	Use of selective potassium channel openers
WO2003105896A1 (en) *	2002-06-14	2003-12-24	Novo Nordisk A/S	Combined use of a modulator of cd3 and a beta cell resting compound
WO2013191984A1 (en) *	2012-06-21	2013-12-27	Boehringer Ingelheim International Gmbh	Fused thiazin-3-ones as kca3.1 inhibitors

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1368948A (en) *	1970-11-11	1974-10-02	Manuf Prod Pharma	Pyridine derivatives
FR2650589A1 (fr) *	1989-08-04	1991-02-08	Esteve Labor Dr	Derives benzothiaziniques, leur preparation et leurs applications comme medicaments ou comme intermediaires de synthese de medicaments
FR2703051B1 (fr) *	1993-03-26	1995-04-28	Adir	Nouvelles pyridothiadiazines, leurs procédés de préparation, et les compositions pharmaceutiques qui les contiennent.

1997
- 1997-01-16 CN CN97191748A patent/CN1208418A/zh active Pending
- 1997-01-16 KR KR1019980705467A patent/KR19990077320A/ko not_active Ceased
- 1997-01-16 EP EP97900933A patent/EP0877748B1/de not_active Expired - Lifetime
- 1997-01-16 RU RU98115386/04A patent/RU2193564C2/ru active
- 1997-01-16 CA CA002241565A patent/CA2241565A1/en not_active Abandoned
- 1997-01-16 CZ CZ982205A patent/CZ220598A3/cs unknown
- 1997-01-16 AT AT97900933T patent/ATE281460T1/de not_active IP Right Cessation
- 1997-01-16 BR BR9707004A patent/BR9707004A/pt unknown
- 1997-01-16 DE DE69731458T patent/DE69731458T2/de not_active Expired - Lifetime
- 1997-01-16 JP JP9525608A patent/JP2000503651A/ja not_active Ceased
- 1997-01-16 PL PL97327927A patent/PL327927A1/xx unknown
- 1997-01-16 WO PCT/DK1997/000018 patent/WO1997026264A1/en not_active Ceased
- 1997-01-16 IL IL12507297A patent/IL125072A/en not_active IP Right Cessation
- 1997-01-16 AU AU14370/97A patent/AU727905B2/en not_active Ceased
- 1997-01-17 US US08/785,435 patent/US5792764A/en not_active Expired - Lifetime
1998
- 1998-07-16 NO NO983285A patent/NO983285L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
CN1208418A (zh)	1999-02-17
NO983285L (no)	1998-09-16
AU1437097A (en)	1997-08-11
NO983285D0 (no)	1998-07-16
BR9707004A (pt)	1999-07-20
PL327927A1 (en)	1999-01-04
RU2193564C2 (ru)	2002-11-27
EP0877748B1 (de)	2004-11-03
WO1997026264A1 (en)	1997-07-24
DE69731458D1 (de)	2004-12-09
JP2000503651A (ja)	2000-03-28
ATE281460T1 (de)	2004-11-15
CA2241565A1 (en)	1997-07-24
KR19990077320A (ko)	1999-10-25
CZ220598A3 (cs)	1998-12-16
EP0877748A1 (de)	1998-11-18
DE69731458T2 (de)	2005-12-22
US5792764A (en)	1998-08-11
AU727905B2 (en)	2001-01-04
IL125072A0 (en)	1999-01-26

Legal Events

Date	Code	Title
2003-05-29	FF	Patent granted
2003-06-24	FF	Patent granted
2005-07-25	MM9K	Patent not in force due to non-payment of renewal fees

Publication	Publication Date	Title
AU727775B2 (en)	2000-12-21	Fused 1,2,4-thiadiazine and fused 1,4-thiazine derivatives, their preparation and use
AU757693B2 (en)	2003-03-06	Fused 1,2,4-thiadiazine derivatives, their preparation and use
US6225310B1 (en)	2001-05-01	Fused 1,2,4-thiadiazine derivatives, their preparation and use
AU737920B2 (en)	2001-09-06	1,2,4-benzothiadiazine derivatives, their preparation and use
EP1338600A1 (de)	2003-08-27	Kondensierte 1,2,4-Thiadiazinderivate, ihre Herstellung und Verwendung
AU727905B2 (en)	2001-01-04	Pyrido-1,2,4-thiadiazine and pyrido-1,4-thiazine derivatives, their preparation and use
WO1999032495A1 (en)	1999-07-01	Pyrido 1,2,4-thiadiazine derivatives, their preparation and use
WO1999032467A1 (en)	1999-07-01	1,2,4-benzothiadiazine derivatives, their preparation and use
RU2199542C2 (ru)	2003-02-27	Производные конденсированного 1,2,4-тиадиазина и конденсированного 1,4-тиазина, их получение и использование
WO1999032494A1 (en)	1999-07-01	Fused 1,2,4-thiadiazine derivatives, their preparation and use
HUP9902648A2 (hu)	2000-02-28	Pirido-1,2,4-tiadiazin- és pirido-1,4-tiazin-származékok, e vagyületek előállítása és alkalmazása, valamint ezeket tartalmazó gyógyászati készítmények
CZ200044A3 (cs)	2000-06-14	Kondenzovaný 1,4-thiazinový derivát, způsob jeho výroby a farmaceutický prostředek ho f obsahující