IE34877L - s-TRIAZINES - Google Patents
s-TRIAZINESInfo
- Publication number
- IE34877L IE34877L IE700421A IE42170A IE34877L IE 34877 L IE34877 L IE 34877L IE 700421 A IE700421 A IE 700421A IE 42170 A IE42170 A IE 42170A IE 34877 L IE34877 L IE 34877L
- Authority
- IE
- Ireland
- Prior art keywords
- alkyl
- compound
- substituted
- triazine
- methyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 abstract 16
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 abstract 10
- -1 bicyclo [2.2.1]heptyl Chemical group 0.000 abstract 10
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 abstract 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 5
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical class C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 abstract 2
- 239000011968 lewis acid catalyst Substances 0.000 abstract 2
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical class NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- BHWDMWAMMZXNJE-UHFFFAOYSA-N 2-N,4-N-bis(2-methylbutan-2-yl)-6-phenoxy-1,3,5-triazine-2,4-diamine Chemical compound O(C1=CC=CC=C1)C1=NC(=NC(=N1)NC(C)(C)CC)NC(C)(C)CC BHWDMWAMMZXNJE-UHFFFAOYSA-N 0.000 abstract 1
- GSLKAMJTXKJXJV-UHFFFAOYSA-N 4,6-bis(2,4,4-trimethylpentan-2-ylamino)-1,3,5-triazine-2-carbonitrile Chemical compound C(#N)C1=NC(=NC(=N1)NC(C)(CC(C)(C)C)C)NC(C)(CC(C)(C)C)C GSLKAMJTXKJXJV-UHFFFAOYSA-N 0.000 abstract 1
- RKMAYERHOYIOBY-UHFFFAOYSA-N 6-chloro-2-n,4-n-bis(2,3,3-trimethylbutan-2-yl)-1,3,5-triazine-2,4-diamine Chemical compound CC(C)(C)C(C)(C)NC1=NC(Cl)=NC(NC(C)(C)C(C)(C)C)=N1 RKMAYERHOYIOBY-UHFFFAOYSA-N 0.000 abstract 1
- SPRRQTAXTOUPFY-UHFFFAOYSA-N 6-chloro-2-n,4-n-bis(2-methylbutan-2-yl)-1,3,5-triazine-2,4-diamine Chemical compound CCC(C)(C)NC1=NC(Cl)=NC(NC(C)(C)CC)=N1 SPRRQTAXTOUPFY-UHFFFAOYSA-N 0.000 abstract 1
- YHVSDOGDOJTVJQ-UHFFFAOYSA-N 6-chloro-2-n,4-n-dicyclohexyl-1,3,5-triazine-2,4-diamine Chemical compound N=1C(NC2CCCCC2)=NC(Cl)=NC=1NC1CCCCC1 YHVSDOGDOJTVJQ-UHFFFAOYSA-N 0.000 abstract 1
- WAQXVFUIWNNVHT-UHFFFAOYSA-N 6-methoxy-2-N,4-N-bis(2,4,4-trimethylpentan-2-yl)-1,3,5-triazine-2,4-diamine Chemical compound COC1=NC(=NC(=N1)NC(C)(CC(C)(C)C)C)NC(C)(CC(C)(C)C)C WAQXVFUIWNNVHT-UHFFFAOYSA-N 0.000 abstract 1
- RJCHAXOLQIAUSP-UHFFFAOYSA-N 6-methylsulfanyl-2-N,4-N-bis(2,4,4-trimethylpentan-2-yl)-1,3,5-triazine-2,4-diamine Chemical compound CSC1=NC(=NC(=N1)NC(C)(CC(C)(C)C)C)NC(C)(CC(C)(C)C)C RJCHAXOLQIAUSP-UHFFFAOYSA-N 0.000 abstract 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 abstract 1
- MKNCFJAVBGHZAF-UHFFFAOYSA-N N-[4-[acetyl(2,4,4-trimethylpentan-2-yl)amino]-6-(2,4,4-trimethylpentan-2-ylamino)-1,3,5-triazin-2-yl]-N-(2,4,4-trimethylpentan-2-yl)acetamide Chemical compound C(C)(=O)N(C1=NC(=NC(=N1)N(C(C)=O)C(C)(CC(C)(C)C)C)NC(C)(CC(C)(C)C)C)C(C)(CC(C)(C)C)C MKNCFJAVBGHZAF-UHFFFAOYSA-N 0.000 abstract 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 239000002585 base Substances 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 1
- 125000004950 trifluoroalkyl group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- 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
- C07D251/26—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 only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/54—Three nitrogen atoms
- C07D251/70—Other substituted melamines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
1308811 s-Triazine derivatives AMERICAN CYANAMID CO 22 May 1970 [22 May 1969 (3)] 24974/70 Heading C2C [Also in Division A5] Novel compounds of Formulµ (a) to (f) wherein R 1 is (C 1 -C 8 ) n-alkyl, (C 4 -C 8 ) secalkyl, (C 4 -C 11 ) tert-alkyl, (C 3 -C 8 ) cycloalkyl or methyl-substituted (C 3 -C 8 ) cycloalkyl; each of R 2 and R 3 is individually (C 4 -C 8 ) sec-alkyl, (C 4 -C 11 ) tert-alkyl, (C 3 -C 8 ) cycloalkyl or methyl-substituted (C 3 -C 8 ) cycloalkyl; R 4 is adamantyl or bicyclo [2.2.1]heptyl; each of R 5 and R 6 is individually (C 1 -C 8 ) n-alkyl, (C 4 -C 8 ) sec-alkyl, (C 4 -C 11 ) tert-alkyl, (C 3 -C 8 ) cycloalkyl, methyl-substituted (C 3 -C 8 ) cycloalkyl, adamantyl, bicyclo [2.2.1]heptyl or methylsubstituted bicyclo [2.2.1]heptyl; R 7 is (C 4 - C 11 ) tert-alkyl, adamantyl, methyl-substituted adamantyl, bicyclo [2.2.1]heptyl or methyl substituted bicyclo [2.2.1]heptyl; R 8 is (C 4 - C 8 ) sec-alkyl, (C 4 -C 11 ) tert-alkyl, (C 3 -C 8 ) cyclo- alkyl, methyl-substituted (C 3 -C 8 ) cycloalkyl, adamantyl, methyl substituted adamantyl, bicyclo [2.2.1]heptyl or methyl-substituted bicyclo [2.2.1]heptyl; each of (R 9 and R 10 ) and (R 11 and R 12 ) are taken together with the nitrogen atom to which they are attached in each instance to form a polymethylene-imino group of from 4 to 6 carbon atoms substituted with from 0 to 4 methyl groups; R 13 is (C 1 -C 8 ) nalkyl, (C 4 -C 8 ) sec-alkyl, (C 3 -C 8 ) cycloalkyl or methyl substituted (C 3 -C 8 ) cycloalkyl; R 14 is (C 1 -C 8 ) n-alkyl or sec-alkyl; and R 15 is methyl substituted adamantyl provided that R 1 , R 2 and R 3 are not identical representing t-butyl, cyclohexyl or 2,4,4-trimethyl-2-pentyl-; or a non- toxic pharmaceutically acceptable salt thereof, are prepared by one of the following methods, (a) a compound of formula wherein each Z is individually chloro, bromo, fluoro, iodo, hydroxyl,-O-alkyl,-O-phenyl, -SH, -S-alkyl, -SO-alkyl, -SO 2 -alkyl- N 3 , -C#N, -N<SP>+</SP>(CH 3 ) 3 , -NH 2 , trichloroalkyl, trifluoroalkyl, guanidino, R-substituted guanidino, NHR or NRR; not more than two of the Z substituents being -NHR and/or -NRR; with a compound of the formula wherein X is -NH 2 , -CO-R, -CHO, -CR=CR, -NHY wherein Y is -CN, -NH 2 , -OH, acyl, sulphonyl, Si(CH 3 ) 3 or a negative charge; -Cl, -Br; F, -I, -OH, -O-alkyl, -O-phenyl, -SH, -S-alkyl, -SO-alkyl, -SO 2 -alkyl, -N 3 , -C#N, -N<SP>+</SP>(CH 3 ) 3 , -NH 2 , -NHR or -NRR; at least one of X and Z containing nitrogen, with the proviso that when X is the same group as Z, X and Z are either -NH 2 or -NHR; R in each case above being selected from R 1 to R 15 such that the compound produced by the reaction is a compound within any one of the Formulµ (a) to (f) above, or when X is -CO-R or CHO, the compound produced by the reaction is reducible to a compound within any one of the Formulµ (a) to (f) above; in the presence or absence of a Lewis acid catalyst in a stepwise manner when the R-substituents on the compound to be produced are different, or in a stepwise and/or concurrent manner when the R- substituents on the compound to be produced are the same; and when X is -CO-R or -CHO, reducing the resulting compound to a compound within any one of the Formulµ (a) to (f) above; (b) when the desired product is a tris-(alkyl-substituted amino)-s-triazine it may be prepared by trimerizing by heat treatment with alkali, a compound of the formula R-C#N; or (c) by reacting a compound of formula wherein Z is defined above, n is 1, 2 or 3 and A and B are chemical valencies which, when taken together form a single bond, or may be bonded to other atoms in a symmetrically or unsymmetrically substituted dimeric or trimeric open chain, with a compound of the formula wherein R and X are each as defined above and the selection of R, X and Z being subject to the same provisos as laid out hereinabove; in the presence or absence of a Lewis acid catalyst, and thereafter, or concurrently, cyclizing the compound produced, or being produced and, when the compound produced is in the form of an iso melamine, isomerizing the isomelamine into an s-triazine of any one of the Formulµ (a) to (f) by treatment with a base. Intermediates isolated in the above processes as exemplified are: 2,4-dichloro-6-(2,2,6,6-tetramethyl - 1 - piperidino) - s - triazine, 6 - chloro- 2,4 - biscyclohexylamino - s - triazine, 2- chloro - 4,6 - bis - (2,3,3 - trimethyl - 2 - butylamino) - s - triazine, 2 - cyano - 4,6 - bis - (2,4,4- trimethyl - 2 - pentylamino) - s - triazine, 2,4- bis - (N - acetyl - 2,4,4 - trimethyl - 2 - pentylamino) - 6 - (2,4,4 - trimethyl - 2 - pentylamino)- s - triazine, 2 - chloro - bis - (tert - pentylamino) - s - triazine, 2 - phenoxy - bis - (tertpentylamino) - s - triazine, 2 - methoxy - bis- (2,4,4 - trimethyl - 2 - pentylamino) - s - triazine and 2 - methylthio - 4,6 - bis - (2,4,4 - trimethyl- 2-pentylamino)-s-triazine. Reference has been directed by the Comptroller to Specification 1,013,223.
[GB1308811A]
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US82703169A | 1969-05-22 | 1969-05-22 | |
| US82704869A | 1969-05-22 | 1969-05-22 | |
| US82703269A | 1969-05-22 | 1969-05-22 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE34877B1 IE34877B1 (en) | 1975-09-17 |
| IE34877L true IE34877L (en) | 1975-09-17 |
Family
ID=27420190
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE700421A IE34877L (en) | 1969-05-22 | 1970-04-03 | s-TRIAZINES |
Country Status (17)
| Country | Link |
|---|---|
| JP (2) | JPS4839945B1 (en) |
| AT (1) | AT306041B (en) |
| BG (1) | BG20376A3 (en) |
| BR (1) | BR6915234D0 (en) |
| CH (1) | CH549589A (en) |
| CS (2) | CS167921B2 (en) |
| DE (1) | DE2025080A1 (en) |
| FR (1) | FR2051553B1 (en) |
| GB (1) | GB1308811A (en) |
| HU (1) | HU164355B (en) |
| IE (1) | IE34877L (en) |
| IL (1) | IL34286A (en) |
| NL (1) | NL7007103A (en) |
| NO (1) | NO128224B (en) |
| OA (1) | OA04242A (en) |
| RO (1) | RO57534A (en) |
| ZM (1) | ZM4370A1 (en) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA791262B (en) * | 1978-04-12 | 1980-07-30 | American Cyanamid Co | Novel anti-arthritic 2,4,6-tris.(substituted-amino)-striazines |
| JPS576367A (en) * | 1980-06-12 | 1982-01-13 | Chubu Electric Power Co Inc | Method for detecting partial discharge of power cable |
| JPS5991376A (en) * | 1982-11-16 | 1984-05-26 | Kansai Electric Power Co Inc:The | Diagnosis of deterioration in insulation of power cable |
| DE3611427A1 (en) * | 1986-04-05 | 1987-10-08 | Hoechst Ag | BIS-TERTIAERBUTYLAMINO-SUBSTITUTED 1,3,5-TRIAZINE DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF, MEDICINAL PRODUCTS CONTAINING THESE COMPOUNDS AND THEIR USE |
| JPS62155323A (en) * | 1986-12-27 | 1987-07-10 | Nippon Seiko Kk | Dynamic pressure type composite bearing device |
| JPS63150914U (en) * | 1987-03-24 | 1988-10-04 | ||
| AT389303B (en) * | 1987-10-08 | 1989-11-27 | Hoechst Ag | Novel bis-tertiary-butylamino-substituted 1,3,5-triazine derivatives, process for their preparation, medicaments containing these compounds, and their use |
| AU621082B2 (en) * | 1988-02-08 | 1992-03-05 | Ciba-Geigy Ag | Tetramethylpiperidino-s-triazines |
| AR036375A1 (en) | 2001-08-30 | 2004-09-01 | Novartis Ag | PIRROLO [2,3-D] PIRIMIDINE -2- CARBONITRILE COMPOUNDS, A PROCESS FOR THEIR PREPARATION, A PHARMACEUTICAL COMPOSITION AND THE USE OF SUCH COMPOUNDS FOR THE PREPARATION OF MEDICINES |
| SE0201976D0 (en) * | 2002-06-24 | 2002-06-24 | Astrazeneca Ab | Novel compounds |
| KR101085157B1 (en) * | 2007-08-31 | 2011-11-18 | 한국화학연구원 | 1,3,5-triazine-2,4,6-triamine compound or a pharmaceutically acceptable salt thereof, and pharmaceutical composition comprising the same |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2691021A (en) * | 1954-10-05 | Trimerization of t |
-
1969
- 1969-12-16 BR BR215234/69A patent/BR6915234D0/en unknown
-
1970
- 1970-04-03 IE IE700421A patent/IE34877L/en unknown
- 1970-04-09 IL IL34286A patent/IL34286A/en unknown
- 1970-04-14 ZM ZM43/70A patent/ZM4370A1/en unknown
- 1970-05-15 NL NL7007103A patent/NL7007103A/xx unknown
- 1970-05-19 RO RO63393A patent/RO57534A/ro unknown
- 1970-05-19 CS CS3481A patent/CS167921B2/cs unknown
- 1970-05-19 CS CS4959*A patent/CS167922B2/cs unknown
- 1970-05-19 BG BG023461A patent/BG20376A3/en unknown
- 1970-05-21 HU HUAE319A patent/HU164355B/hu unknown
- 1970-05-21 NO NO01944/70A patent/NO128224B/no unknown
- 1970-05-21 CH CH753270A patent/CH549589A/en not_active IP Right Cessation
- 1970-05-22 DE DE19702025080 patent/DE2025080A1/en not_active Withdrawn
- 1970-05-22 JP JP45043955A patent/JPS4839945B1/ja active Pending
- 1970-05-22 AT AT463170A patent/AT306041B/en not_active IP Right Cessation
- 1970-05-22 FR FR7018738A patent/FR2051553B1/fr not_active Expired
- 1970-05-22 GB GB2497470A patent/GB1308811A/en not_active Expired
- 1970-05-22 OA OA53930A patent/OA04242A/en unknown
-
1971
- 1971-12-23 JP JP46105126A patent/JPS4917272B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| BR6915234D0 (en) | 1973-06-07 |
| IL34286A (en) | 1974-03-14 |
| IL34286A0 (en) | 1970-12-24 |
| DE2025080A1 (en) | 1970-11-26 |
| NL7007103A (en) | 1970-11-24 |
| IE34877B1 (en) | 1975-09-17 |
| CS167922B2 (en) | 1976-05-28 |
| JPS4839945B1 (en) | 1973-11-28 |
| AT306041B (en) | 1973-03-26 |
| OA04242A (en) | 1979-12-31 |
| CS167921B2 (en) | 1976-05-28 |
| FR2051553A1 (en) | 1971-04-09 |
| ZM4370A1 (en) | 1971-02-22 |
| GB1308811A (en) | 1973-03-07 |
| CH549589A (en) | 1974-05-31 |
| JPS4917272B1 (en) | 1974-04-27 |
| RO57534A (en) | 1975-01-15 |
| HU164355B (en) | 1974-02-28 |
| FR2051553B1 (en) | 1976-04-16 |
| NO128224B (en) | 1973-10-15 |
| BG20376A3 (en) | 1975-11-05 |
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