NO301274B1 - Benzotiazolderivater, deres anvendelse, og farmakologiske preparater omfattende slike - Google Patents
Benzotiazolderivater, deres anvendelse, og farmakologiske preparater omfattende slike Download PDFInfo
- Publication number
- NO301274B1 NO301274B1 NO921282A NO921282A NO301274B1 NO 301274 B1 NO301274 B1 NO 301274B1 NO 921282 A NO921282 A NO 921282A NO 921282 A NO921282 A NO 921282A NO 301274 B1 NO301274 B1 NO 301274B1
- Authority
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- Norway
- Prior art keywords
- formula
- stated
- group
- pharmacologically tolerable
- tolerable salt
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- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 title claims abstract description 44
- 238000002360 preparation method Methods 0.000 title claims description 15
- 230000000144 pharmacologic effect Effects 0.000 title claims description 11
- 150000003839 salts Chemical class 0.000 claims abstract description 42
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 41
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 40
- 238000004519 manufacturing process Methods 0.000 claims abstract description 31
- 239000003814 drug Substances 0.000 claims abstract description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 18
- 150000002617 leukotrienes Chemical class 0.000 claims abstract description 14
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 12
- 201000010099 disease Diseases 0.000 claims abstract description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 11
- 150000003595 thromboxanes Chemical class 0.000 claims abstract description 10
- 125000002252 acyl group Chemical group 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 7
- 230000000694 effects Effects 0.000 claims description 13
- 238000003786 synthesis reaction Methods 0.000 claims description 13
- 230000015572 biosynthetic process Effects 0.000 claims description 12
- 229940079593 drug Drugs 0.000 claims description 12
- 108010069102 Thromboxane-A synthase Proteins 0.000 claims description 9
- 102000001381 Arachidonate 5-Lipoxygenase Human genes 0.000 claims description 7
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- 206010009900 Colitis ulcerative Diseases 0.000 claims description 5
- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 5
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 4
- RZWIIPASKMUIAC-VQTJNVASSA-N thromboxane group Chemical group CCCCCCC[C@H]1CCCO[C@@H]1CCCCCCCC RZWIIPASKMUIAC-VQTJNVASSA-N 0.000 claims description 3
- 229940124125 5 Lipoxygenase inhibitor Drugs 0.000 claims 1
- 239000000867 Lipoxygenase Inhibitor Substances 0.000 claims 1
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- -1 6-hydroxy-5,7-dimethyl-2-(3-pyridylmethyl)-aminobenzothiazole 6-hydroxy-4,5,7-trimethyl -2-(3-pyridylmethyl)-aminobenzothiazole 6-hydroxy-4,7-dimethyl-2-(3-pyridylmethyl)-aminobenzothiazole Chemical compound 0.000 description 32
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- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920001289 polyvinyl ether Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 description 1
- 229960005205 prednisolone Drugs 0.000 description 1
- QJZUKDFHGGYHMC-UHFFFAOYSA-N pyridine-3-carbaldehyde Chemical compound O=CC1=CC=CN=C1 QJZUKDFHGGYHMC-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 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
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 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
- 230000002123 temporal effect Effects 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
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 230000000451 tissue damage Effects 0.000 description 1
- 231100000827 tissue damage Toxicity 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
- 231100000820 toxicity test Toxicity 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 235000013337 tricalcium citrate Nutrition 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D417/06—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 carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles 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 in position 2
- C07D277/82—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Dental Preparations (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7148091 | 1991-04-04 | ||
| JP28136691 | 1991-10-28 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO921282D0 NO921282D0 (no) | 1992-04-02 |
| NO921282L NO921282L (no) | 1992-10-05 |
| NO301274B1 true NO301274B1 (no) | 1997-10-06 |
Family
ID=26412577
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO921282A NO301274B1 (no) | 1991-04-04 | 1992-04-02 | Benzotiazolderivater, deres anvendelse, og farmakologiske preparater omfattende slike |
Country Status (19)
| Country | Link |
|---|---|
| US (3) | US5300518A (hu) |
| EP (1) | EP0507318B1 (hu) |
| KR (1) | KR970000954B1 (hu) |
| CN (1) | CN1030451C (hu) |
| AT (1) | ATE157976T1 (hu) |
| AU (1) | AU658868B2 (hu) |
| CA (1) | CA2064992A1 (hu) |
| DE (1) | DE69222076T2 (hu) |
| DK (1) | DK0507318T3 (hu) |
| ES (1) | ES2104761T3 (hu) |
| FI (1) | FI921303A (hu) |
| GR (1) | GR3024867T3 (hu) |
| HU (1) | HU219448B (hu) |
| IE (1) | IE920921A1 (hu) |
| MX (1) | MX9201544A (hu) |
| NO (1) | NO301274B1 (hu) |
| NZ (1) | NZ242204A (hu) |
| PH (1) | PH30229A (hu) |
| TW (1) | TW198031B (hu) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5296486A (en) * | 1991-09-24 | 1994-03-22 | Boehringer Ingelheim Pharmaceuticals, Inc. | Leukotriene biosynthesis inhibitors |
| EP0704435B1 (en) * | 1993-07-30 | 1998-06-24 | Eisai Co., Ltd. | Process for producing hydroquinone and benzoquinone derivative |
| GB9605065D0 (en) * | 1996-03-11 | 1996-05-08 | Merck Sharp & Dohme | Therapeutic agents |
| CA2309711C (en) | 1997-11-11 | 2003-09-16 | Nikken Chemicals Co., Ltd. | N-hydroxyurea derivative and pharmaceutical composition containing the same |
| US6794397B2 (en) * | 2000-01-27 | 2004-09-21 | Cytovia, Inc. | Substituted nicotinamides and analogs as activators of caspases and inducers of apoptosis and the use thereof |
| JP2005512957A (ja) * | 2001-08-13 | 2005-05-12 | マックス−プランク−ゲゼルシャフト ツール フェルデルンク デル ヴィッセンシャフテン エー．ファウ． | ポリｑ−凝集の阻害剤 |
| CN103360339B (zh) * | 2013-08-13 | 2015-05-13 | 安徽工业大学 | 一种绿色催化合成2′-氨基苯并噻唑-芳甲基-2-萘酚的方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1931077A (en) * | 1931-08-05 | 1933-10-17 | Du Pont | 1-amino-5-methoxy-benzo-thiazole |
| US4873346A (en) * | 1985-09-20 | 1989-10-10 | The Upjohn Company | Substituted benzothiazoles, benzimidazoles, and benzoxazoles |
| US4763346A (en) * | 1986-06-27 | 1988-08-09 | Eastman Kodak Company | Photographic cassette and method of dispensing |
| FI91859C (fi) * | 1987-06-17 | 1994-08-25 | Eisai Co Ltd | Analogiamenetelmä antiallergisena aineena aktiivisen bentsotiatsolijohdannaisen valmistamiseksi |
| GB8820231D0 (en) * | 1988-08-25 | 1988-09-28 | Fujisawa Pharmaceutical Co | New benzazole compounds processes for preparation thereof & pharmaceutical composition comprising same |
-
1992
- 1992-03-23 IE IE092192A patent/IE920921A1/en not_active IP Right Cessation
- 1992-03-25 FI FI921303A patent/FI921303A/fi unknown
- 1992-03-30 PH PH44133A patent/PH30229A/en unknown
- 1992-03-31 US US07/861,379 patent/US5300518A/en not_active Expired - Lifetime
- 1992-04-01 TW TW08112483A patent/TW198031B/zh active
- 1992-04-02 AU AU13990/92A patent/AU658868B2/en not_active Ceased
- 1992-04-02 CA CA002064992A patent/CA2064992A1/en not_active Abandoned
- 1992-04-02 NO NO921282A patent/NO301274B1/no not_active IP Right Cessation
- 1992-04-02 NZ NZ242204A patent/NZ242204A/en unknown
- 1992-04-03 EP EP92105777A patent/EP0507318B1/en not_active Expired - Lifetime
- 1992-04-03 ES ES92105777T patent/ES2104761T3/es not_active Expired - Lifetime
- 1992-04-03 DK DK92105777.4T patent/DK0507318T3/da active
- 1992-04-03 DE DE69222076T patent/DE69222076T2/de not_active Expired - Fee Related
- 1992-04-03 HU HU9201141A patent/HU219448B/hu not_active IP Right Cessation
- 1992-04-03 MX MX9201544A patent/MX9201544A/es unknown
- 1992-04-03 AT AT92105777T patent/ATE157976T1/de not_active IP Right Cessation
- 1992-04-04 KR KR1019920005646A patent/KR970000954B1/ko not_active IP Right Cessation
- 1992-04-04 CN CN92102349A patent/CN1030451C/zh not_active Expired - Fee Related
-
1993
- 1993-11-05 US US08/148,914 patent/US5420144A/en not_active Expired - Lifetime
-
1995
- 1995-02-15 US US08/388,813 patent/US5635519A/en not_active Expired - Lifetime
-
1997
- 1997-09-25 GR GR970402510T patent/GR3024867T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU658868B2 (en) | 1995-05-04 |
| EP0507318B1 (en) | 1997-09-10 |
| KR970000954B1 (ko) | 1997-01-21 |
| MX9201544A (es) | 1992-10-01 |
| IE920921A1 (en) | 1992-10-07 |
| FI921303A (fi) | 1992-10-05 |
| NZ242204A (en) | 1995-02-24 |
| NO921282D0 (no) | 1992-04-02 |
| HU9201141D0 (en) | 1992-06-29 |
| TW198031B (hu) | 1993-01-11 |
| HUT62890A (en) | 1993-06-28 |
| DK0507318T3 (da) | 1998-03-23 |
| PH30229A (en) | 1997-02-05 |
| HU219448B (hu) | 2001-04-28 |
| CA2064992A1 (en) | 1992-10-05 |
| FI921303A0 (fi) | 1992-03-25 |
| ATE157976T1 (de) | 1997-09-15 |
| DE69222076T2 (de) | 1998-02-19 |
| US5420144A (en) | 1995-05-30 |
| US5300518A (en) | 1994-04-05 |
| ES2104761T3 (es) | 1997-10-16 |
| DE69222076D1 (de) | 1997-10-16 |
| GR3024867T3 (en) | 1998-01-30 |
| AU1399092A (en) | 1992-10-08 |
| NO921282L (no) | 1992-10-05 |
| US5635519A (en) | 1997-06-03 |
| EP0507318A1 (en) | 1992-10-07 |
| CN1065457A (zh) | 1992-10-21 |
| KR920019785A (ko) | 1992-11-20 |
| CN1030451C (zh) | 1995-12-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM1K | Lapsed by not paying the annual fees |