NL7908287A - Triazinonen. - Google Patents
Triazinonen. Download PDFInfo
- Publication number
- NL7908287A NL7908287A NL7908287A NL7908287A NL7908287A NL 7908287 A NL7908287 A NL 7908287A NL 7908287 A NL7908287 A NL 7908287A NL 7908287 A NL7908287 A NL 7908287A NL 7908287 A NL7908287 A NL 7908287A
- Authority
- NL
- Netherlands
- Prior art keywords
- triazinone
- dihydro
- pharmaceutically acceptable
- lower alkyl
- acceptable salts
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims description 95
- 125000000217 alkyl group Chemical group 0.000 claims description 49
- SQSPRWMERUQXNE-UHFFFAOYSA-N Guanylurea Chemical compound NC(=N)NC(N)=O SQSPRWMERUQXNE-UHFFFAOYSA-N 0.000 claims description 39
- 150000003839 salts Chemical class 0.000 claims description 37
- -1 cyano, carboxyl Chemical group 0.000 claims description 36
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 35
- 231100000252 nontoxic Toxicity 0.000 claims description 29
- 230000003000 nontoxic effect Effects 0.000 claims description 29
- 239000003153 chemical reaction reagent Substances 0.000 claims description 25
- 238000002360 preparation method Methods 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 21
- 229910052736 halogen Inorganic materials 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 230000001142 anti-diarrhea Effects 0.000 claims description 19
- OKGXJRGLYVRVNE-UHFFFAOYSA-N diaminomethylidenethiourea Chemical compound NC(N)=NC(N)=S OKGXJRGLYVRVNE-UHFFFAOYSA-N 0.000 claims description 19
- 150000002367 halogens Chemical class 0.000 claims description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 125000001931 aliphatic group Chemical group 0.000 claims description 14
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 239000001301 oxygen Substances 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 150000001408 amides Chemical class 0.000 claims description 12
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 11
- 229910052717 sulfur Chemical group 0.000 claims description 11
- 239000011593 sulfur Chemical group 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 9
- 230000001262 anti-secretory effect Effects 0.000 claims description 9
- 125000004076 pyridyl group Chemical group 0.000 claims description 9
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 8
- 239000002168 alkylating agent Substances 0.000 claims description 7
- 229940100198 alkylating agent Drugs 0.000 claims description 7
- 125000001118 alkylidene group Chemical group 0.000 claims description 7
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 6
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
- 125000004423 acyloxy group Chemical group 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- 125000004442 acylamino group Chemical group 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
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- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
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- 238000004519 manufacturing process Methods 0.000 claims 5
- 150000002431 hydrogen Chemical class 0.000 claims 3
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 235000011114 ammonium hydroxide Nutrition 0.000 claims 2
- 150000008378 aryl ethers Chemical group 0.000 claims 2
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000001589 carboacyl group Chemical group 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 238000012360 testing method Methods 0.000 description 38
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 17
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 125000004432 carbon atom Chemical group C* 0.000 description 13
- 238000007363 ring formation reaction Methods 0.000 description 13
- 125000001424 substituent group Chemical group 0.000 description 13
- 150000003918 triazines Chemical class 0.000 description 13
- 239000000243 solution Substances 0.000 description 12
- OPOJRMTZHYUKLY-UHFFFAOYSA-N 1h-1,3,5-triazin-2-one Chemical class O=C1N=CN=CN1 OPOJRMTZHYUKLY-UHFFFAOYSA-N 0.000 description 11
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- 239000003589 local anesthetic agent Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 10
- 241001465754 Metazoa Species 0.000 description 9
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- 238000002347 injection Methods 0.000 description 8
- 235000012054 meals Nutrition 0.000 description 8
- UZHSEJADLWPNLE-GRGSLBFTSA-N naloxone Chemical compound O=C([C@@H]1O2)CC[C@@]3(O)[C@H]4CC5=CC=C(O)C2=C5[C@@]13CCN4CC=C UZHSEJADLWPNLE-GRGSLBFTSA-N 0.000 description 8
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- 230000000144 pharmacologic effect Effects 0.000 description 8
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
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- SPEUIVXLLWOEMJ-UHFFFAOYSA-N acetaldehyde dimethyl acetal Natural products COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 5
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- HYPPXZBJBPSRLK-UHFFFAOYSA-N diphenoxylate Chemical compound C1CC(C(=O)OCC)(C=2C=CC=CC=2)CCN1CCC(C#N)(C=1C=CC=CC=1)C1=CC=CC=C1 HYPPXZBJBPSRLK-UHFFFAOYSA-N 0.000 description 5
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- UYXAWHWODHRRMR-UHFFFAOYSA-N hexobarbital Chemical compound O=C1N(C)C(=O)NC(=O)C1(C)C1=CCCCC1 UYXAWHWODHRRMR-UHFFFAOYSA-N 0.000 description 5
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- 239000007928 intraperitoneal injection Substances 0.000 description 5
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 5
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
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- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/16—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom
-
- 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
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/10—Laxatives
-
- 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
- A61P1/12—Antidiarrhoeals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US95961178 | 1978-11-13 | ||
| US05/959,611 US4246409A (en) | 1978-11-13 | 1978-11-13 | Triazinones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL7908287A true NL7908287A (nl) | 1980-05-16 |
Family
ID=25502213
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL7908287A NL7908287A (nl) | 1978-11-13 | 1979-11-13 | Triazinonen. |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4246409A (en, 2012) |
| JP (1) | JPS5572174A (en, 2012) |
| AR (1) | AR226547A1 (en, 2012) |
| AU (1) | AU530790B2 (en, 2012) |
| BE (1) | BE879990A (en, 2012) |
| CA (1) | CA1136136A (en, 2012) |
| CH (1) | CH647515A5 (en, 2012) |
| DE (1) | DE2945701A1 (en, 2012) |
| ES (1) | ES485929A0 (en, 2012) |
| FR (1) | FR2441617A1 (en, 2012) |
| GB (1) | GB2039891B (en, 2012) |
| HU (1) | HU180289B (en, 2012) |
| IT (1) | IT1193334B (en, 2012) |
| MX (1) | MX6832E (en, 2012) |
| NL (1) | NL7908287A (en, 2012) |
| PH (1) | PH17430A (en, 2012) |
| ZA (1) | ZA796079B (en, 2012) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4387225A (en) * | 1981-01-15 | 1983-06-07 | William H. Rorer, Inc. | Heterocyclic alkylene triazinones |
| US4452980A (en) * | 1981-01-15 | 1984-06-05 | William H. Rorer, Inc. | Triazinones |
| US4443456A (en) * | 1981-05-12 | 1984-04-17 | William H. Rorer, Inc. | Pyridyl alkylene amidinoureas |
| US4460585A (en) * | 1981-07-06 | 1984-07-17 | William H. Rorer, Inc. | 1-Aryl-4-hydrazinyl-s-triazin-2-ones |
| US4406897A (en) * | 1981-07-06 | 1983-09-27 | William H. Rorer, Inc. | 6-Aryl-4-hydrazinyl-s-triazin-2-ones |
| USRE33125E (en) * | 1981-07-06 | 1989-12-05 | Rorer Pharmaceutical Corporation | 3- and 5-[3-(1-arylureido)]-1,2,4-triazoles |
| EP0073276A1 (en) * | 1981-08-24 | 1983-03-09 | Rorer International (Overseas) Inc. | A method of increasing the feed efficiency of animals, and compositions for use in such a method |
| US4562188A (en) * | 1984-01-13 | 1985-12-31 | William H. Rorer, Inc. | Triazinones for treating irritable bowel syndrome |
| WO2011109383A1 (en) * | 2010-03-02 | 2011-09-09 | Southern Research Institute | Use of 2'-deoxy -4'-thiocytidine and its analogues as dna hypomethylating anticancer agents |
| WO2015050212A1 (ja) * | 2013-10-02 | 2015-04-09 | 日産化学工業株式会社 | Ｔ型カルシウムチャネル阻害剤 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1287910A (en, 2012) * | 1968-12-19 | 1972-09-06 | ||
| IL42103A (en) * | 1972-05-24 | 1976-05-31 | Du Pont | 6-amino-s-triazine-2,4-(1h,3h)-diones and corresponding 4-thio compounds,their preparation and their use as herbicides |
| US4068081A (en) * | 1974-02-15 | 1978-01-10 | Imperial Chemical Industries Limited | Δ-Triazine-2,6-dione |
-
1978
- 1978-11-13 US US05/959,611 patent/US4246409A/en not_active Expired - Lifetime
-
1979
- 1979-11-07 CA CA000339405A patent/CA1136136A/en not_active Expired
- 1979-11-12 PH PH23273A patent/PH17430A/en unknown
- 1979-11-12 AU AU52735/79A patent/AU530790B2/en not_active Ceased
- 1979-11-12 ZA ZA00796079A patent/ZA796079B/xx unknown
- 1979-11-13 MX MX798483U patent/MX6832E/es unknown
- 1979-11-13 BE BE0/198083A patent/BE879990A/fr not_active IP Right Cessation
- 1979-11-13 DE DE19792945701 patent/DE2945701A1/de not_active Ceased
- 1979-11-13 HU HU79RO1042A patent/HU180289B/hu unknown
- 1979-11-13 GB GB7939190A patent/GB2039891B/en not_active Expired
- 1979-11-13 ES ES485929A patent/ES485929A0/es active Granted
- 1979-11-13 NL NL7908287A patent/NL7908287A/nl not_active Application Discontinuation
- 1979-11-13 CH CH10138/79A patent/CH647515A5/de not_active IP Right Cessation
- 1979-11-13 IT IT27243/79A patent/IT1193334B/it active
- 1979-11-13 JP JP14697079A patent/JPS5572174A/ja active Granted
- 1979-11-13 FR FR7927874A patent/FR2441617A1/fr active Granted
- 1979-11-18 AR AR278877A patent/AR226547A1/es active
Also Published As
| Publication number | Publication date |
|---|---|
| AU530790B2 (en) | 1983-07-28 |
| GB2039891A (en) | 1980-08-20 |
| IT7927243A0 (it) | 1979-11-13 |
| ZA796079B (en) | 1980-12-31 |
| US4246409A (en) | 1981-01-20 |
| CA1136136A (en) | 1982-11-23 |
| PH17430A (en) | 1984-08-20 |
| ES8100278A1 (es) | 1980-11-01 |
| MX6832E (es) | 1986-08-15 |
| BE879990A (fr) | 1980-05-13 |
| CH647515A5 (de) | 1985-01-31 |
| FR2441617B1 (en, 2012) | 1983-08-26 |
| AU5273579A (en) | 1980-05-22 |
| ES485929A0 (es) | 1980-11-01 |
| AR226547A1 (es) | 1982-07-30 |
| IT1193334B (it) | 1988-06-15 |
| JPS5572174A (en) | 1980-05-30 |
| JPS6365664B2 (en, 2012) | 1988-12-16 |
| DE2945701A1 (de) | 1980-08-07 |
| HU180289B (en) | 1983-02-28 |
| FR2441617A1 (fr) | 1980-06-13 |
| GB2039891B (en) | 1983-05-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A85 | Still pending on 85-01-01 | ||
| BA | A request for search or an international-type search has been filed | ||
| BB | A search report has been drawn up | ||
| BC | A request for examination has been filed | ||
| BV | The patent application has lapsed |