FR2493844A1 - Nouvelles 5-(phenyl facultativement substitue)-6h-1,3,4-thiadiazine-2-amines, utiles notamment comme relaxants musculaires, et leur procede de preparation - Google Patents
Nouvelles 5-(phenyl facultativement substitue)-6h-1,3,4-thiadiazine-2-amines, utiles notamment comme relaxants musculaires, et leur procede de preparation Download PDFInfo
- Publication number
- FR2493844A1 FR2493844A1 FR8024049A FR8024049A FR2493844A1 FR 2493844 A1 FR2493844 A1 FR 2493844A1 FR 8024049 A FR8024049 A FR 8024049A FR 8024049 A FR8024049 A FR 8024049A FR 2493844 A1 FR2493844 A1 FR 2493844A1
- Authority
- FR
- France
- Prior art keywords
- thiadiazine
- amine
- dichlorophenyl
- methanol
- opt
- 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
- 239000003158 myorelaxant agent Substances 0.000 title claims abstract description 10
- 229940035363 muscle relaxants Drugs 0.000 title claims abstract description 5
- 241001465754 Metazoa Species 0.000 title abstract description 4
- WNLXZSXQMYFYHG-UHFFFAOYSA-N 2h-1,3,4-thiadiazin-2-amine Chemical compound NC1SC=CN=N1 WNLXZSXQMYFYHG-UHFFFAOYSA-N 0.000 title description 2
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 15
- 239000002253 acid Substances 0.000 claims abstract description 6
- 150000003839 salts Chemical class 0.000 claims abstract description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 25
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- 239000004480 active ingredient Substances 0.000 claims description 6
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- 238000000034 method Methods 0.000 claims description 4
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- 238000002360 preparation method Methods 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
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- 150000001412 amines Chemical class 0.000 claims 2
- BGHDMGYBBOCDIQ-UHFFFAOYSA-N 5-(4-fluorophenyl)-n-methyl-6h-1,3,4-thiadiazin-2-amine Chemical compound C1SC(NC)=NN=C1C1=CC=C(F)C=C1 BGHDMGYBBOCDIQ-UHFFFAOYSA-N 0.000 claims 1
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 10
- 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 abstract description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract description 3
- 229960004782 chlordiazepoxide Drugs 0.000 abstract description 3
- JZFICWYCTCCINF-UHFFFAOYSA-N Thiadiazin Chemical compound S=C1SC(C)NC(C)N1CCN1C(=S)SC(C)NC1C JZFICWYCTCCINF-UHFFFAOYSA-N 0.000 abstract 1
- 229940035676 analgesics Drugs 0.000 abstract 1
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- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 239000003443 antiviral agent Substances 0.000 abstract 1
- 229940121357 antivirals Drugs 0.000 abstract 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 abstract 1
- 125000001153 fluoro group Chemical group F* 0.000 abstract 1
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- 239000002904 solvent Substances 0.000 description 4
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- 230000000694 effects Effects 0.000 description 3
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- 239000001257 hydrogen Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
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- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- ZJEKBPWVIUDJKX-UHFFFAOYSA-N n-methyl-5-phenyl-6h-1,3,4-thiadiazin-2-amine Chemical compound C1SC(NC)=NN=C1C1=CC=CC=C1 ZJEKBPWVIUDJKX-UHFFFAOYSA-N 0.000 description 1
- MUEYRHLSJVIHHW-UHFFFAOYSA-N n-methyl-5-phenyl-6h-1,3,4-thiadiazin-2-amine;hydrochloride Chemical compound Cl.C1SC(NC)=NN=C1C1=CC=CC=C1 MUEYRHLSJVIHHW-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000011514 reflex Effects 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
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 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
- ORGHESHFQPYLAO-UHFFFAOYSA-N vinyl radical Chemical compound C=[CH] ORGHESHFQPYLAO-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/15—Six-membered rings
- C07D285/16—Thiadiazines; Hydrogenated thiadiazines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8024049A FR2493844A1 (fr) | 1980-11-12 | 1980-11-12 | Nouvelles 5-(phenyl facultativement substitue)-6h-1,3,4-thiadiazine-2-amines, utiles notamment comme relaxants musculaires, et leur procede de preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8024049A FR2493844A1 (fr) | 1980-11-12 | 1980-11-12 | Nouvelles 5-(phenyl facultativement substitue)-6h-1,3,4-thiadiazine-2-amines, utiles notamment comme relaxants musculaires, et leur procede de preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2493844A1 true FR2493844A1 (fr) | 1982-05-14 |
| FR2493844B1 FR2493844B1 (cg-RX-API-DMAC7.html) | 1983-07-08 |
Family
ID=9247890
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8024049A Granted FR2493844A1 (fr) | 1980-11-12 | 1980-11-12 | Nouvelles 5-(phenyl facultativement substitue)-6h-1,3,4-thiadiazine-2-amines, utiles notamment comme relaxants musculaires, et leur procede de preparation |
Country Status (1)
| Country | Link |
|---|---|
| FR (1) | FR2493844A1 (cg-RX-API-DMAC7.html) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1992018484A1 (en) * | 1991-04-12 | 1992-10-29 | A.H. Robins Company, Incorporated | 3-amino-5-arylpyrazole-4-acetic acid derivatives exhibiting therapeutic effects |
| US6028068A (en) * | 1995-12-28 | 2000-02-22 | The Procter & Gamble Company | Substituted 6H-1,3,4-thiadiazine-2-amines, the use thereof as anaesthetising, cardiovascular and hypometabolic agents, and a pharmaceutical composition containing them |
| US6117867A (en) * | 1995-12-28 | 2000-09-12 | Procter & Gamble Company | Substituted 6-R-1,3,4-thiadiazine-2-amines, the use thereof as anaesthetizing, cardiovascular and hypometabolic agents, and a pharmaceutical composition containing them |
| US6313111B1 (en) | 1995-12-28 | 2001-11-06 | The Procter & Gamble Company | Substituted 6H-1,3,4-thiadiazine-2-amines, the use thereof as anaesthetising, cardiovascular and hypometabolic agents, and pharmaceutical composition containing them |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2058066A (en) * | 1979-09-04 | 1981-04-08 | Richardson Merrell Inc | 6h-1,3,4-thiadiazine-2-amines |
-
1980
- 1980-11-12 FR FR8024049A patent/FR2493844A1/fr active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2058066A (en) * | 1979-09-04 | 1981-04-08 | Richardson Merrell Inc | 6h-1,3,4-thiadiazine-2-amines |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1992018484A1 (en) * | 1991-04-12 | 1992-10-29 | A.H. Robins Company, Incorporated | 3-amino-5-arylpyrazole-4-acetic acid derivatives exhibiting therapeutic effects |
| US6028068A (en) * | 1995-12-28 | 2000-02-22 | The Procter & Gamble Company | Substituted 6H-1,3,4-thiadiazine-2-amines, the use thereof as anaesthetising, cardiovascular and hypometabolic agents, and a pharmaceutical composition containing them |
| US6117867A (en) * | 1995-12-28 | 2000-09-12 | Procter & Gamble Company | Substituted 6-R-1,3,4-thiadiazine-2-amines, the use thereof as anaesthetizing, cardiovascular and hypometabolic agents, and a pharmaceutical composition containing them |
| US6313111B1 (en) | 1995-12-28 | 2001-11-06 | The Procter & Gamble Company | Substituted 6H-1,3,4-thiadiazine-2-amines, the use thereof as anaesthetising, cardiovascular and hypometabolic agents, and pharmaceutical composition containing them |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2493844B1 (cg-RX-API-DMAC7.html) | 1983-07-08 |
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