GB1308811A - Triazine derivatives - Google Patents
Triazine derivativesInfo
- Publication number
- GB1308811A GB1308811A GB2497470A GB2497470A GB1308811A GB 1308811 A GB1308811 A GB 1308811A GB 2497470 A GB2497470 A GB 2497470A GB 2497470 A GB2497470 A GB 2497470A GB 1308811 A GB1308811 A GB 1308811A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- compound
- substituted
- triazine
- methyl
- 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.)
- Expired
Links
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.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US82704869A | 1969-05-22 | 1969-05-22 | |
US82703169A | 1969-05-22 | 1969-05-22 | |
US82703269A | 1969-05-22 | 1969-05-22 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1308811A true GB1308811A (en) | 1973-03-07 |
Family
ID=27420190
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB2497470A Expired GB1308811A (en) | 1969-05-22 | 1970-05-22 | Triazine derivatives |
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) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7112589B2 (en) | 2001-08-30 | 2006-09-26 | Novartis Ag | Cysteine protease inhibitors with 2-cyano-4-amino-pyrimidine structure and cathepsin k inhibitory activity for the treatment of inflammations and other diseases |
Families Citing this family (10)
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 |
SE0201976D0 (en) * | 2002-06-24 | 2002-06-24 | Astrazeneca Ab | Novel compounds |
EP2197858B1 (en) * | 2007-08-31 | 2014-07-02 | HanAll Biopharma Co., Ltd. | 1,3,5-triazine-2,4,6-triamine compound or pharmaceutical 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 BG BG23461A patent/BG20376A3/xx unknown
- 1970-05-19 CS CS3481A patent/CS167921B2/cs unknown
- 1970-05-19 CS CS4959*A patent/CS167922B2/cs unknown
- 1970-05-21 NO NO01944/70A patent/NO128224B/no unknown
- 1970-05-21 CH CH753270A patent/CH549589A/en not_active IP Right Cessation
- 1970-05-21 HU HUAE319A patent/HU164355B/hu unknown
- 1970-05-22 GB GB2497470A patent/GB1308811A/en not_active Expired
- 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 OA OA53930A patent/OA04242A/en unknown
- 1970-05-22 FR FR7018738A patent/FR2051553B1/fr not_active Expired
- 1970-05-22 DE DE19702025080 patent/DE2025080A1/en not_active Withdrawn
-
1971
- 1971-12-23 JP JP46105126A patent/JPS4917272B1/ja active Pending
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7112589B2 (en) | 2001-08-30 | 2006-09-26 | Novartis Ag | Cysteine protease inhibitors with 2-cyano-4-amino-pyrimidine structure and cathepsin k inhibitory activity for the treatment of inflammations and other diseases |
Also Published As
Publication number | Publication date |
---|---|
OA04242A (en) | 1979-12-31 |
DE2025080A1 (en) | 1970-11-26 |
CS167922B2 (en) | 1976-05-28 |
FR2051553B1 (en) | 1976-04-16 |
ZM4370A1 (en) | 1971-02-22 |
CH549589A (en) | 1974-05-31 |
BR6915234D0 (en) | 1973-06-07 |
NO128224B (en) | 1973-10-15 |
JPS4839945B1 (en) | 1973-11-28 |
IE34877B1 (en) | 1975-09-17 |
BG20376A3 (en) | 1975-11-05 |
CS167921B2 (en) | 1976-05-28 |
FR2051553A1 (en) | 1971-04-09 |
HU164355B (en) | 1974-02-28 |
NL7007103A (en) | 1970-11-24 |
AT306041B (en) | 1973-03-26 |
IL34286A (en) | 1974-03-14 |
JPS4917272B1 (en) | 1974-04-27 |
RO57534A (en) | 1975-01-15 |
IE34877L (en) | 1975-09-17 |
IL34286A0 (en) | 1970-12-24 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PS | Patent sealed [section 19, patents act 1949] | ||
PCNP | Patent ceased through non-payment of renewal fee |