FR2485531A1 - Nouveaux n-oxydes de diaryl-5,6 as triazines 1-2-4, leur application a titre de medicaments et les compositions pharmaceutiques les contenant - Google Patents
Nouveaux n-oxydes de diaryl-5,6 as triazines 1-2-4, leur application a titre de medicaments et les compositions pharmaceutiques les contenant Download PDFInfo
- Publication number
- FR2485531A1 FR2485531A1 FR8014106A FR8014106A FR2485531A1 FR 2485531 A1 FR2485531 A1 FR 2485531A1 FR 8014106 A FR8014106 A FR 8014106A FR 8014106 A FR8014106 A FR 8014106A FR 2485531 A1 FR2485531 A1 FR 2485531A1
- Authority
- FR
- France
- Prior art keywords
- oxide
- triazine
- phenyl
- diparamethoxy
- piperazino
- Prior art date
- Legal status (The legal status 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 status listed.)
- Granted
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 4
- 239000003814 drug Substances 0.000 title claims 2
- 150000003918 triazines Chemical class 0.000 title abstract description 4
- 229940079593 drug Drugs 0.000 title 1
- -1 PIPERAZINO Chemical class 0.000 claims abstract description 49
- 150000001875 compounds Chemical class 0.000 claims abstract description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 150000002367 halogens Chemical class 0.000 claims abstract description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 3
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 claims description 74
- 150000001204 N-oxides Chemical class 0.000 claims description 74
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 43
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
- 125000000815 N-oxide group Chemical group 0.000 claims description 2
- 230000000202 analgesic effect Effects 0.000 claims description 2
- 230000002744 anti-aggregatory effect Effects 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims 1
- YUXBNNVWBUTOQZ-UHFFFAOYSA-N 4-phenyltriazine Chemical compound C1=CC=CC=C1C1=CC=NN=N1 YUXBNNVWBUTOQZ-UHFFFAOYSA-N 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical compound C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 abstract description 3
- 230000001225 therapeutic effect Effects 0.000 abstract description 3
- 208000019695 Migraine disease Diseases 0.000 abstract description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- CPEONABTMRSIKA-UHFFFAOYSA-N 1,4$l^{2}-oxazinane Chemical class C1COCC[N]1 CPEONABTMRSIKA-UHFFFAOYSA-N 0.000 abstract 1
- 241001237754 Algia Species 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical class [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 206010027599 migraine Diseases 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 51
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 43
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 40
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- 238000000034 method Methods 0.000 description 26
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- 238000002844 melting Methods 0.000 description 23
- 230000008018 melting Effects 0.000 description 23
- 239000000377 silicon dioxide Substances 0.000 description 21
- 239000002904 solvent Substances 0.000 description 21
- 239000013078 crystal Substances 0.000 description 20
- 238000002329 infrared spectrum Methods 0.000 description 20
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 9
- 239000000543 intermediate Substances 0.000 description 8
- 0 **(*C1I=*)=C(c(cc2)ccc2O)C(c2ccc(*I)cc2)=I11ICC1 Chemical compound **(*C1I=*)=C(c(cc2)ccc2O)C(c2ccc(*I)cc2)=I11ICC1 0.000 description 5
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- 231100000636 lethal dose Toxicity 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
- RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 description 1
- WRXNJTBODVGDRY-UHFFFAOYSA-N 2-pyrrolidin-1-ylethanamine Chemical compound NCCN1CCCC1 WRXNJTBODVGDRY-UHFFFAOYSA-N 0.000 description 1
- WGTASENVNYJZBK-UHFFFAOYSA-N 3,4,5-trimethoxyamphetamine Chemical compound COC1=CC(CC(C)N)=CC(OC)=C1OC WGTASENVNYJZBK-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- BZFKSWOGZQMOMO-UHFFFAOYSA-N 3-chloropropan-1-amine Chemical compound NCCCCl BZFKSWOGZQMOMO-UHFFFAOYSA-N 0.000 description 1
- ZNKKYYNWFKHNHZ-UHFFFAOYSA-N CC1C=CC=CC1 Chemical compound CC1C=CC=CC1 ZNKKYYNWFKHNHZ-UHFFFAOYSA-N 0.000 description 1
- 241000639544 Dipara Species 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 229920002565 Polyethylene Glycol 400 Polymers 0.000 description 1
- IFFPICMESYHZPQ-UHFFFAOYSA-N Prenylamine Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)CCNC(C)CC1=CC=CC=C1 IFFPICMESYHZPQ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 244000062793 Sorghum vulgare Species 0.000 description 1
- 230000004931 aggregating effect Effects 0.000 description 1
- 230000001618 algogenic effect Effects 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000004181 carboxyalkyl group Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- GWOFUCIGLDBNKM-UHFFFAOYSA-N glafenine Chemical compound OCC(O)COC(=O)C1=CC=CC=C1NC1=CC=NC2=CC(Cl)=CC=C12 GWOFUCIGLDBNKM-UHFFFAOYSA-N 0.000 description 1
- 229960001650 glafenine Drugs 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 description 1
- RWIVICVCHVMHMU-UHFFFAOYSA-N n-aminoethylmorpholine Chemical compound NCCN1CCOCC1 RWIVICVCHVMHMU-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229960001989 prenylamine Drugs 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 231100000041 toxicology testing Toxicity 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
- C07D253/06—1,2,4-Triazines
- C07D253/065—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
- C07D253/06—1,2,4-Triazines
- C07D253/065—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
- C07D253/07—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8014106A FR2485531A1 (fr) | 1980-06-25 | 1980-06-25 | Nouveaux n-oxydes de diaryl-5,6 as triazines 1-2-4, leur application a titre de medicaments et les compositions pharmaceutiques les contenant |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8014106A FR2485531A1 (fr) | 1980-06-25 | 1980-06-25 | Nouveaux n-oxydes de diaryl-5,6 as triazines 1-2-4, leur application a titre de medicaments et les compositions pharmaceutiques les contenant |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2485531A1 true FR2485531A1 (fr) | 1981-12-31 |
| FR2485531B1 FR2485531B1 (enExample) | 1983-09-23 |
Family
ID=9243502
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8014106A Granted FR2485531A1 (fr) | 1980-06-25 | 1980-06-25 | Nouveaux n-oxydes de diaryl-5,6 as triazines 1-2-4, leur application a titre de medicaments et les compositions pharmaceutiques les contenant |
Country Status (1)
| Country | Link |
|---|---|
| FR (1) | FR2485531A1 (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007536353A (ja) * | 2004-05-05 | 2007-12-13 | ピエール ファーブル デルモ−コスメティック | ５，６−ジフェニル−１，２，４−トリアジンの単量体誘導体と該誘導体の利用 |
| WO2011095625A1 (en) | 2010-02-05 | 2011-08-11 | Heptares Therapeutics Limited | 1,2,4-triazine-4-amine derivatives |
| CN104812747A (zh) * | 2012-10-01 | 2015-07-29 | 国家科学研究中心 | 用于治疗病毒感染的1,2,4-三嗪衍生物 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111989313A (zh) * | 2018-02-15 | 2020-11-24 | 杭州阿诺生物医药科技有限公司 | A2a和/或a2b受体拮抗剂 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH480795A (de) * | 1967-03-01 | 1969-11-15 | Sandoz Ag | Mittel zur Beeinflussung des Pflanzenwachstums |
| US3948894A (en) * | 1974-01-31 | 1976-04-06 | Eli Lilly And Company | 3-Amino-5,6-diaryl-1,2,4-triazines |
| FR2391202A1 (fr) * | 1977-05-17 | 1978-12-15 | Diamond Shamrock Corp | Triazines-1,2,4 substituees, actives pharmacologiquement et medicaments contenant ces triazines |
-
1980
- 1980-06-25 FR FR8014106A patent/FR2485531A1/fr active Granted
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH480795A (de) * | 1967-03-01 | 1969-11-15 | Sandoz Ag | Mittel zur Beeinflussung des Pflanzenwachstums |
| US3948894A (en) * | 1974-01-31 | 1976-04-06 | Eli Lilly And Company | 3-Amino-5,6-diaryl-1,2,4-triazines |
| FR2391202A1 (fr) * | 1977-05-17 | 1978-12-15 | Diamond Shamrock Corp | Triazines-1,2,4 substituees, actives pharmacologiquement et medicaments contenant ces triazines |
Non-Patent Citations (3)
| Title |
|---|
| CA1967 * |
| EXBK/66 * |
| EXBK/69 * |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007536353A (ja) * | 2004-05-05 | 2007-12-13 | ピエール ファーブル デルモ−コスメティック | ５，６−ジフェニル−１，２，４−トリアジンの単量体誘導体と該誘導体の利用 |
| WO2011095625A1 (en) | 2010-02-05 | 2011-08-11 | Heptares Therapeutics Limited | 1,2,4-triazine-4-amine derivatives |
| US8809525B2 (en) | 2010-02-05 | 2014-08-19 | Heptares Therapeutics Limited | 1,2,4-triazine-4-amine derivatives |
| US9249130B2 (en) | 2010-02-05 | 2016-02-02 | Heptares Therapeutics Limited | 1,2,4-triazine-4-amine derivatives |
| US10112923B2 (en) | 2010-02-05 | 2018-10-30 | Heptares Therapeutics Limited | 1,2,4-triazine-4-amine derivatives |
| US10988455B2 (en) | 2010-02-05 | 2021-04-27 | Heptares Therapeutics Limited | 1,2,4-triazine-4-amine derivatives |
| US12054472B2 (en) | 2010-02-05 | 2024-08-06 | Nxera Pharma Uk Limited | 1,2,4-triazine-4-amine derivatives |
| CN104812747A (zh) * | 2012-10-01 | 2015-07-29 | 国家科学研究中心 | 用于治疗病毒感染的1,2,4-三嗪衍生物 |
| CN104812747B (zh) * | 2012-10-01 | 2017-03-08 | 国家科学研究中心 | 用于治疗病毒感染的1,2,4‑三嗪衍生物 |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2485531B1 (enExample) | 1983-09-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |