NO316913B1 - Benzotiadiazoler og derivater - Google Patents
Benzotiadiazoler og derivater Download PDFInfo
- Publication number
- NO316913B1 NO316913B1 NO20003916A NO20003916A NO316913B1 NO 316913 B1 NO316913 B1 NO 316913B1 NO 20003916 A NO20003916 A NO 20003916A NO 20003916 A NO20003916 A NO 20003916A NO 316913 B1 NO316913 B1 NO 316913B1
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- Prior art keywords
- compound
- formula
- alkyl
- free base
- acid addition
- Prior art date
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- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical class C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 46
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 150000003839 salts Chemical group 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 12
- 239000012458 free base Substances 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
- 201000010099 disease Diseases 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 239000008024 pharmaceutical diluent Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 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 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 102000012289 Corticotropin-Releasing Hormone Human genes 0.000 description 14
- 108010022152 Corticotropin-Releasing Hormone Proteins 0.000 description 14
- 239000000055 Corticotropin-Releasing Hormone Substances 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 230000003042 antagnostic effect Effects 0.000 description 3
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- BRZYSWJRSDMWLG-CAXSIQPQSA-N geneticin Chemical compound O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](C(C)O)O2)N)[C@@H](N)C[C@H]1N BRZYSWJRSDMWLG-CAXSIQPQSA-N 0.000 description 3
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- SGVCZSZADFJNOL-UHFFFAOYSA-N 4-(6-chloro-2,5-dimethylpyrimidin-4-yl)-5,7-dimethyl-2,1,3-benzothiadiazol-6-amine Chemical compound CC1=NC(Cl)=C(C)C(C=2C3=NSN=C3C(C)=C(N)C=2C)=N1 SGVCZSZADFJNOL-UHFFFAOYSA-N 0.000 description 2
- 208000024827 Alzheimer disease Diseases 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
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- 229910052794 bromium Inorganic materials 0.000 description 2
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- 238000000338 in vitro Methods 0.000 description 2
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- 238000012360 testing method Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- FWWOWPGPERBCNJ-UHFFFAOYSA-N 2-hydroxy-4-(2-hydroxyethoxy)-4-oxobutanoic acid Chemical compound OCCOC(=O)CC(O)C(O)=O FWWOWPGPERBCNJ-UHFFFAOYSA-N 0.000 description 1
- IUFNOGBUZVGTBC-UHFFFAOYSA-N 4,5-dichloro-2,5-dimethyl-4h-pyrimidine Chemical compound CC1=NC(Cl)C(C)(Cl)C=N1 IUFNOGBUZVGTBC-UHFFFAOYSA-N 0.000 description 1
- DSUGVVQJCVIUIV-UHFFFAOYSA-N 4,6-dimethyl-2,1,3-benzothiadiazole Chemical compound C1=C(C)C=C(C)C2=NSN=C21 DSUGVVQJCVIUIV-UHFFFAOYSA-N 0.000 description 1
- FDIMQEBEDLZCIQ-UHFFFAOYSA-N 5,7-dimethyl-4-nitro-2,1,3-benzothiadiazole Chemical compound [O-][N+](=O)C1=C(C)C=C(C)C2=NSN=C21 FDIMQEBEDLZCIQ-UHFFFAOYSA-N 0.000 description 1
- 229930024421 Adenine Natural products 0.000 description 1
- GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 description 1
- 208000000103 Anorexia Nervosa Diseases 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
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- 241000699802 Cricetulus griseus Species 0.000 description 1
- 208000011231 Crohn disease Diseases 0.000 description 1
- IVOMOUWHDPKRLL-KQYNXXCUSA-N Cyclic adenosine monophosphate Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-KQYNXXCUSA-N 0.000 description 1
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- 241000282412 Homo Species 0.000 description 1
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- 206010065390 Inflammatory pain Diseases 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
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- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
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- 238000004113 cell culture Methods 0.000 description 1
- ANTSCNMPPGJYLG-UHFFFAOYSA-N chlordiazepoxide Chemical compound O=N=1CC(NC)=NC2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 ANTSCNMPPGJYLG-UHFFFAOYSA-N 0.000 description 1
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- VZCYOOQTPOCHFL-OWOJBTEDSA-M fumarate(1-) Chemical compound OC(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-M 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
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- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/40—Benzopyrazines
- C07D241/44—Benzopyrazines with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
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- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/14—Thiadiazoles; Hydrogenated thiadiazoles condensed with carbocyclic rings or ring systems
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- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D473/32—Nitrogen atom
- C07D473/34—Nitrogen atom attached in position 6, e.g. adenine
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- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9802251.0A GB9802251D0 (en) | 1998-02-03 | 1998-02-03 | Organic compounds |
| PCT/EP1999/000622 WO1999040089A1 (en) | 1998-02-03 | 1999-02-01 | Benzothiadiazoles and derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20003916D0 NO20003916D0 (no) | 2000-08-02 |
| NO20003916L NO20003916L (no) | 2000-09-28 |
| NO316913B1 true NO316913B1 (no) | 2004-06-21 |
Family
ID=10826354
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20003916A NO316913B1 (no) | 1998-02-03 | 2000-08-02 | Benzotiadiazoler og derivater |
Country Status (30)
| Country | Link |
|---|---|
| EP (1) | EP1049694B1 (hu) |
| JP (1) | JP3455180B2 (hu) |
| KR (2) | KR100502880B1 (hu) |
| CN (1) | CN1119346C (hu) |
| AR (1) | AR015222A1 (hu) |
| AT (1) | ATE217622T1 (hu) |
| AU (1) | AU745051B2 (hu) |
| BR (1) | BR9909739A (hu) |
| CA (1) | CA2318977A1 (hu) |
| CO (1) | CO4990932A1 (hu) |
| DE (1) | DE69901483T2 (hu) |
| DK (1) | DK1049694T3 (hu) |
| ES (1) | ES2178451T3 (hu) |
| GB (1) | GB9802251D0 (hu) |
| HK (1) | HK1033578A1 (hu) |
| HU (1) | HUP0100978A3 (hu) |
| ID (1) | ID26156A (hu) |
| IL (1) | IL137332A (hu) |
| MY (1) | MY122453A (hu) |
| NO (1) | NO316913B1 (hu) |
| NZ (1) | NZ505970A (hu) |
| PE (1) | PE20000246A1 (hu) |
| PL (1) | PL194838B1 (hu) |
| PT (1) | PT1049694E (hu) |
| RU (1) | RU2219177C2 (hu) |
| SK (1) | SK283833B6 (hu) |
| TR (1) | TR200002237T2 (hu) |
| TW (1) | TW509689B (hu) |
| WO (1) | WO1999040089A1 (hu) |
| ZA (1) | ZA99800B (hu) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| IL139197A0 (en) * | 1999-10-29 | 2001-11-25 | Pfizer Prod Inc | Use of corticotropin releasing factor antagonists and related compositions |
| PE20030008A1 (es) | 2001-06-19 | 2003-01-22 | Bristol Myers Squibb Co | Inhibidores duales de pde 7 y pde 4 |
| GB0302876D0 (en) * | 2003-02-07 | 2003-03-12 | Novartis Ag | Organic compounds |
| CN104383542B (zh) | 2003-04-08 | 2017-09-26 | 普罗热尼奇制药公司 | 包含甲基纳曲酮的药物配方 |
| AR057035A1 (es) | 2005-05-25 | 2007-11-14 | Progenics Pharm Inc | SíNTESIS DE (R)-N-METILNALTREXONA, COMPOSICIONES FARMACÉUTICAS Y USOS |
| AR057325A1 (es) | 2005-05-25 | 2007-11-28 | Progenics Pharm Inc | Sintesis de (s)-n-metilnaltrexona, composiciones farmaceuticas y usos |
| GB0525068D0 (en) | 2005-12-08 | 2006-01-18 | Novartis Ag | Organic compounds |
| WO2007149938A2 (en) | 2006-06-21 | 2007-12-27 | The Salk Institute Biological Studies | Methods for promoting hair growth |
| EP3263571B2 (en) | 2007-03-29 | 2023-08-23 | Progenics Pharmaceuticals, Inc. | Crystal form of (r)-n-methylnaltrexone bromide and uses thereof |
| US8338446B2 (en) | 2007-03-29 | 2012-12-25 | Wyeth Llc | Peripheral opioid receptor antagonists and uses thereof |
| PE20130480A1 (es) | 2007-03-29 | 2013-05-08 | Progenics Pharm Inc | Compuestos heterociclicos como antagonistas del receptor opioide periferico |
| WO2009099411A1 (en) | 2008-02-06 | 2009-08-13 | Progenics Pharmaceuticals, Inc. | Preparation and use of (r),(r)-2,2'-bis-methylnaltrexone |
| CA2676881C (en) | 2008-09-30 | 2017-04-25 | Wyeth | Peripheral opioid receptor antagonists and uses thereof |
| US8349852B2 (en) | 2009-01-13 | 2013-01-08 | Novartis Ag | Quinazolinone derivatives useful as vanilloid antagonists |
| US20120295942A1 (en) | 2010-02-01 | 2012-11-22 | Nicholas James Devereux | Pyrazolo[5,1b]oxazole Derivatives as CRF-1 Receptor Antagonists |
| WO2011092293A2 (en) | 2010-02-01 | 2011-08-04 | Novartis Ag | Cyclohexyl amide derivatives as crf receptor antagonists |
| ES2527849T3 (es) | 2010-02-02 | 2015-01-30 | Novartis Ag | Derivados de ciclohexilamida como antagonistas del receptor de CRF |
| AR086554A1 (es) | 2011-05-27 | 2014-01-08 | Novartis Ag | Derivados de la piperidina 3-espirociclica como agonistas de receptores de la ghrelina |
| CN104271579A (zh) | 2012-05-03 | 2015-01-07 | 诺华股份有限公司 | 作为生长素释放肽受体激动剂的2,7-二氮杂-螺[4,5]癸烷-7-基衍生物的l-苹果酸盐及其结晶 |
| CA3039026A1 (en) | 2016-09-07 | 2018-03-15 | The Regents Of The University Of California | Allosteric corticotropin-releasing factor receptor 1 (crfr1) antagonists that decrease p-tau and improve cognition |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2499991A1 (fr) * | 1981-02-19 | 1982-08-20 | Sandoz Sa | Nouveaux 2,1,3-benzothiadiazoles et 2,1,3-benzoxadiazoles, leur preparation et leur application comme medicaments |
| KR0163624B1 (ko) * | 1992-04-28 | 1998-12-01 | 오노다 마사요시 | 신규의 치환된 3급 아미노 화합물 또는 이의 염 |
| GB9323290D0 (en) * | 1992-12-10 | 1994-01-05 | Zeneca Ltd | Quinazoline derivatives |
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1998
- 1998-02-03 GB GBGB9802251.0A patent/GB9802251D0/en not_active Ceased
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1999
- 1999-01-27 CO CO99004377A patent/CO4990932A1/es unknown
- 1999-01-29 MY MYPI99000329A patent/MY122453A/en unknown
- 1999-02-01 KR KR10-2004-7015274A patent/KR100502880B1/ko not_active IP Right Cessation
- 1999-02-01 DK DK99934200T patent/DK1049694T3/da active
- 1999-02-01 HU HU0100978A patent/HUP0100978A3/hu unknown
- 1999-02-01 CA CA002318977A patent/CA2318977A1/en not_active Abandoned
- 1999-02-01 PE PE1999000070A patent/PE20000246A1/es not_active Application Discontinuation
- 1999-02-01 AU AU32521/99A patent/AU745051B2/en not_active Ceased
- 1999-02-01 EP EP99934200A patent/EP1049694B1/en not_active Expired - Lifetime
- 1999-02-01 AR ARP990100410A patent/AR015222A1/es not_active Application Discontinuation
- 1999-02-01 KR KR10-2000-7008418A patent/KR100507250B1/ko not_active IP Right Cessation
- 1999-02-01 DE DE69901483T patent/DE69901483T2/de not_active Expired - Lifetime
- 1999-02-01 PL PL342008A patent/PL194838B1/pl not_active IP Right Cessation
- 1999-02-01 TR TR2000/02237T patent/TR200002237T2/xx unknown
- 1999-02-01 ES ES99934200T patent/ES2178451T3/es not_active Expired - Lifetime
- 1999-02-01 ID IDW20001473A patent/ID26156A/id unknown
- 1999-02-01 NZ NZ505970A patent/NZ505970A/xx unknown
- 1999-02-01 BR BR9909739-7A patent/BR9909739A/pt not_active Application Discontinuation
- 1999-02-01 PT PT99934200T patent/PT1049694E/pt unknown
- 1999-02-01 JP JP2000530518A patent/JP3455180B2/ja not_active Expired - Fee Related
- 1999-02-01 AT AT99934200T patent/ATE217622T1/de not_active IP Right Cessation
- 1999-02-01 SK SK1157-2000A patent/SK283833B6/sk unknown
- 1999-02-01 IL IL13733299A patent/IL137332A/xx active IP Right Grant
- 1999-02-01 WO PCT/EP1999/000622 patent/WO1999040089A1/en not_active Application Discontinuation
- 1999-02-01 RU RU2000123169/04A patent/RU2219177C2/ru not_active IP Right Cessation
- 1999-02-01 CN CN99802662A patent/CN1119346C/zh not_active Expired - Fee Related
- 1999-02-02 ZA ZA9900800A patent/ZA99800B/xx unknown
- 1999-02-24 TW TW088102726A patent/TW509689B/zh not_active IP Right Cessation
-
2000
- 2000-08-02 NO NO20003916A patent/NO316913B1/no unknown
-
2001
- 2001-04-18 HK HK01102751A patent/HK1033578A1/xx not_active IP Right Cessation
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