GB1498629A - Pyridylalkyl derivatives of urea and thiourea - Google Patents
Pyridylalkyl derivatives of urea and thioureaInfo
- Publication number
- GB1498629A GB1498629A GB5542274A GB5542274A GB1498629A GB 1498629 A GB1498629 A GB 1498629A GB 5542274 A GB5542274 A GB 5542274A GB 5542274 A GB5542274 A GB 5542274A GB 1498629 A GB1498629 A GB 1498629A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydrocarbyl
- halo
- alkoxy
- compound
- aryl
- 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
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 title abstract 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 title abstract 2
- 150000003672 ureas Chemical class 0.000 title abstract 2
- 125000001475 halogen functional group Chemical group 0.000 abstract 7
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 6
- 125000003545 alkoxy group Chemical group 0.000 abstract 5
- 125000003118 aryl group Chemical group 0.000 abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 5
- 125000004414 alkyl thio group Chemical group 0.000 abstract 3
- 125000004442 acylamino group Chemical group 0.000 abstract 2
- 125000003282 alkyl amino group Chemical group 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 2
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000005110 aryl thio group Chemical group 0.000 abstract 1
- 125000004104 aryloxy group Chemical group 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 229940094443 oxytocics prostaglandins Drugs 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 150000003180 prostaglandins Chemical class 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000004953 trihalomethyl group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/40—Acylated substituent nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1498629 Pyridylalkyl derivatives of urea and thiourea UPJOHN CO 23 Dec 1974 [26 Dec 1973] 55422/74 Heading C2C Novel compounds I and II (R 1 and R 2 are H, halo, 1-6C hydrocarbyl, alkoxy, alkylthio, NO 2 , amino, alkylamino, dialkylamino, acylamino or trihalomethyl; R 3 and R 4 are H, hydrocarbyl or aryl optionally substituted by halo, NO 2 , 1-4C alkoxy, or hydrocarbyl ; R 5 and R 6 are H, halo, hydrocarbyl, halo - hydrocarbyl, NO 2 , CN, amino, acylamino, alkylamino, dialkylamino, alkylthio, alkoxy, arylthio or aryloxy; X is O or S and n is 1 or 2, with the provisos that, in Formula II, (1) when R 1 , R 2 , R 4 , R 5 and R 6 are H and X is S that R 3 is H, cycloalkyl, aryl, aralkyl or aryl substituted by halo, NO 2 , 1-4C alkoxy or hydrocarbyl; (2) when R 1 and R 2 are H or halo: R 4 , R 5 and R 6 are H and X is O, that R 3 is 1-4C alkyl, cycloalkyl, aryl, aralkyl, or aryl substituted by halo, NO 2 , 1-4C alkoxy or hydrocarbyl; and (3) when R 1 , R 2 , R 3 , R 4 and R 6 are H, X is O and n is 1, that R 5 is not CF 3 , NO 2 , CN or alkylthio) and pharmaceutically acceptable salts thereof are prepared by known methods, e.g. by reaction of a compound IV with a compound V or by reaction of a compound VIII with a compound IX followed where necessary by N-oxidation. Pharmaceutical compositions comprise a compound I or II together with the usual carriers and are useful in increasing the production of endogenous prostaglandins.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US42837273A | 1973-12-26 | 1973-12-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1498629A true GB1498629A (en) | 1978-01-25 |
Family
ID=23698610
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5542274A Expired GB1498629A (en) | 1973-12-26 | 1974-12-23 | Pyridylalkyl derivatives of urea and thiourea |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS5095276A (en) |
| DE (1) | DE2460780A1 (en) |
| FR (1) | FR2255902B1 (en) |
| GB (1) | GB1498629A (en) |
| NL (1) | NL7416238A (en) |
-
1974
- 1974-12-13 NL NL7416238A patent/NL7416238A/en not_active Application Discontinuation
- 1974-12-20 JP JP14581774A patent/JPS5095276A/ja active Pending
- 1974-12-21 DE DE19742460780 patent/DE2460780A1/en active Pending
- 1974-12-23 GB GB5542274A patent/GB1498629A/en not_active Expired
- 1974-12-24 FR FR7442758A patent/FR2255902B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2255902A1 (en) | 1975-07-25 |
| FR2255902B1 (en) | 1978-07-28 |
| JPS5095276A (en) | 1975-07-29 |
| NL7416238A (en) | 1975-06-30 |
| DE2460780A1 (en) | 1975-07-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |