DE2800385A1 - Tetrahydro-1,2,4-triazine, verfahren zur herstellung von 3-substituierten tetrahydro-1,2,4-triazinen sowie deren verwendung - Google Patents
Tetrahydro-1,2,4-triazine, verfahren zur herstellung von 3-substituierten tetrahydro-1,2,4-triazinen sowie deren verwendungInfo
- Publication number
- DE2800385A1 DE2800385A1 DE19782800385 DE2800385A DE2800385A1 DE 2800385 A1 DE2800385 A1 DE 2800385A1 DE 19782800385 DE19782800385 DE 19782800385 DE 2800385 A DE2800385 A DE 2800385A DE 2800385 A1 DE2800385 A1 DE 2800385A1
- Authority
- DE
- Germany
- Prior art keywords
- phenyl
- tetrahydro
- group
- triazine
- aminoethylhydrazine
- 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
- -1 3-SUBSTITUTED TETRAHYDRO-1,2,4-TRIAZINE Chemical class 0.000 title claims description 37
- 238000000034 method Methods 0.000 title claims description 30
- 230000008569 process Effects 0.000 title claims description 15
- 238000002360 preparation method Methods 0.000 title claims description 11
- MKVBVTOSWPBSNC-UHFFFAOYSA-N 1,2,3,4-tetrahydro-1,2,4-triazine Chemical compound C1NNC=CN1 MKVBVTOSWPBSNC-UHFFFAOYSA-N 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 49
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 45
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 22
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 150000002825 nitriles Chemical class 0.000 claims description 15
- JHKIHARISAHZAK-UHFFFAOYSA-N 2-hydrazinylethanamine Chemical class NCCNN JHKIHARISAHZAK-UHFFFAOYSA-N 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 208000019901 Anxiety disease Diseases 0.000 claims description 8
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 8
- 230000036506 anxiety Effects 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 230000003197 catalytic effect Effects 0.000 claims description 6
- 229910052723 transition metal Inorganic materials 0.000 claims description 6
- DRONDEZXOJEUGU-UHFFFAOYSA-N 2,3-diphenylpropanenitrile Chemical group C=1C=CC=CC=1C(C#N)CC1=CC=CC=C1 DRONDEZXOJEUGU-UHFFFAOYSA-N 0.000 claims description 5
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 230000021736 acetylation Effects 0.000 claims description 2
- 238000006640 acetylation reaction Methods 0.000 claims description 2
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 claims description 2
- 229940073608 benzyl chloride Drugs 0.000 claims description 2
- 230000011987 methylation Effects 0.000 claims description 2
- 238000007069 methylation reaction Methods 0.000 claims description 2
- HOSLYCHCJBOEKW-UHFFFAOYSA-N 3-[2-(4-chlorophenyl)-1-phenylethyl]-1,2,5,6-tetrahydro-1,2,4-triazine Chemical compound C1=CC(Cl)=CC=C1CC(C=1C=CC=CC=1)C1=NNCCN1 HOSLYCHCJBOEKW-UHFFFAOYSA-N 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 229910052717 sulfur Inorganic materials 0.000 description 9
- 239000011593 sulfur Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
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- UTBDLWOYFNBYNE-UHFFFAOYSA-N 1,2,4-triazine;hydrochloride Chemical compound Cl.C1=CN=NC=N1 UTBDLWOYFNBYNE-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
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- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical class C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 2
- QQZDRBLYFGVUER-UHFFFAOYSA-N 3-(1,2-diphenylethyl)-1,2,5,6-tetrahydro-1,2,4-triazine Chemical compound C=1C=CC=CC=1CC(C=1C=CC=CC=1)C1=NCCNN1 QQZDRBLYFGVUER-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
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- 238000002347 injection Methods 0.000 description 2
- 239000007928 intraperitoneal injection Substances 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
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- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 description 1
- OYEHFRMFJLFNSD-UHFFFAOYSA-N 1,2,5,6-tetrahydro-1,2,4-triazine Chemical class C1CN=CNN1 OYEHFRMFJLFNSD-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- FUFLCEKSBBHCMO-UHFFFAOYSA-N 11-dehydrocorticosterone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 FUFLCEKSBBHCMO-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
- YQUAOWNIIVZNAK-UHFFFAOYSA-N 3-(1,2-diphenylethyl)-1,2,5,6-tetrahydro-1,2,4-triazine;hydrochloride Chemical compound Cl.C=1C=CC=CC=1CC(C=1C=CC=CC=1)C1=NNCCN1 YQUAOWNIIVZNAK-UHFFFAOYSA-N 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
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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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Anesthesiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/761,177 US4071684A (en) | 1977-01-21 | 1977-01-21 | Process for producing 3-substituted 1,2,4-triazines |
| US05/803,927 US4263295A (en) | 1977-06-06 | 1977-06-06 | Psychoactive 3-(1-2-diarylethyl)-1,4,5,6-tetrahydro-1,2,4-triazines and their method of use |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2800385A1 true DE2800385A1 (de) | 1978-07-27 |
| DE2800385C2 DE2800385C2 (en, 2012) | 1989-01-26 |
Family
ID=27116938
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19782800385 Granted DE2800385A1 (de) | 1977-01-21 | 1978-01-05 | Tetrahydro-1,2,4-triazine, verfahren zur herstellung von 3-substituierten tetrahydro-1,2,4-triazinen sowie deren verwendung |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS5395987A (en, 2012) |
| AT (1) | AT360032B (en, 2012) |
| CH (1) | CH639080A5 (en, 2012) |
| DE (1) | DE2800385A1 (en, 2012) |
| DK (1) | DK152755C (en, 2012) |
| ES (1) | ES466205A1 (en, 2012) |
| FR (1) | FR2378019A1 (en, 2012) |
| GB (1) | GB1576579A (en, 2012) |
| IE (1) | IE46246B1 (en, 2012) |
| IT (1) | IT1111157B (en, 2012) |
| NL (1) | NL7800535A (en, 2012) |
| NO (1) | NO159529C (en, 2012) |
| SE (1) | SE447380B (en, 2012) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3471486A (en) * | 1967-10-23 | 1969-10-07 | Dow Chemical Co | 3-aralkyl-as-triazines |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3497509A (en) * | 1966-12-05 | 1970-02-24 | Dow Chemical Co | Imino ester method for producing 1,4,5,6-tetrahydro-as-triazine |
| US3428635A (en) * | 1966-12-05 | 1969-02-18 | Dow Chemical Co | Substituted 1,4,5,6 - tetrahydro - as - triazines and a method for their production |
-
1978
- 1978-01-05 DE DE19782800385 patent/DE2800385A1/de active Granted
- 1978-01-17 DK DK023078A patent/DK152755C/da not_active IP Right Cessation
- 1978-01-17 NL NL7800535A patent/NL7800535A/xx not_active Application Discontinuation
- 1978-01-18 IE IE115/78A patent/IE46246B1/en not_active IP Right Cessation
- 1978-01-19 IT IT19422/78A patent/IT1111157B/it active
- 1978-01-19 JP JP378478A patent/JPS5395987A/ja active Granted
- 1978-01-19 NO NO78780201A patent/NO159529C/no unknown
- 1978-01-20 FR FR7801672A patent/FR2378019A1/fr active Granted
- 1978-01-20 ES ES466205A patent/ES466205A1/es not_active Expired
- 1978-01-20 AT AT44378A patent/AT360032B/de not_active IP Right Cessation
- 1978-01-20 SE SE7800737A patent/SE447380B/sv not_active IP Right Cessation
- 1978-01-20 GB GB2389/78A patent/GB1576579A/en not_active Expired
- 1978-01-20 CH CH65378A patent/CH639080A5/fr not_active IP Right Cessation
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3471486A (en) * | 1967-10-23 | 1969-10-07 | Dow Chemical Co | 3-aralkyl-as-triazines |
Also Published As
| Publication number | Publication date |
|---|---|
| NO159529C (no) | 1989-01-11 |
| IT7819422A0 (it) | 1978-01-19 |
| SE447380B (sv) | 1986-11-10 |
| CH639080A5 (en) | 1983-10-31 |
| IE780115L (en) | 1978-07-21 |
| FR2378019A1 (fr) | 1978-08-18 |
| IT1111157B (it) | 1986-01-13 |
| ES466205A1 (es) | 1979-06-01 |
| DK152755B (da) | 1988-05-09 |
| SE7800737L (sv) | 1978-07-22 |
| DK152755C (da) | 1988-10-03 |
| FR2378019B1 (en, 2012) | 1980-08-22 |
| JPS5395987A (en) | 1978-08-22 |
| NO159529B (no) | 1988-10-03 |
| JPS6241227B2 (en, 2012) | 1987-09-02 |
| DE2800385C2 (en, 2012) | 1989-01-26 |
| NL7800535A (nl) | 1978-07-25 |
| GB1576579A (en) | 1980-10-08 |
| NO780201L (no) | 1978-07-24 |
| ATA44378A (de) | 1980-05-15 |
| IE46246B1 (en) | 1983-04-06 |
| DK23078A (da) | 1978-07-22 |
| AT360032B (de) | 1980-12-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |