GB1287317A - Novel adamantylurea derivatives and a process for the preparation thereof - Google Patents
Novel adamantylurea derivatives and a process for the preparation thereofInfo
- Publication number
- GB1287317A GB1287317A GB5049070A GB5049070A GB1287317A GB 1287317 A GB1287317 A GB 1287317A GB 5049070 A GB5049070 A GB 5049070A GB 5049070 A GB5049070 A GB 5049070A GB 1287317 A GB1287317 A GB 1287317A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compounds
- formula
- adamantyl
- alkyl
- reacting
- 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
- QYYHPAUOLCHORH-UHFFFAOYSA-N 1-adamantylurea Chemical class C1C(C2)CC3CC2CC1(NC(=O)N)C3 QYYHPAUOLCHORH-UHFFFAOYSA-N 0.000 title abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 10
- 125000000217 alkyl group Chemical group 0.000 abstract 7
- -1 1 - adamantyl Chemical group 0.000 abstract 5
- 239000003960 organic solvent Substances 0.000 abstract 4
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 abstract 3
- 229910052799 carbon Inorganic materials 0.000 abstract 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 abstract 2
- XWEBGYHDYSOANZ-UHFFFAOYSA-N 2-(pentylamino)acetic acid;hydrochloride Chemical compound Cl.CCCCCNCC(O)=O XWEBGYHDYSOANZ-UHFFFAOYSA-N 0.000 abstract 1
- UYSWGJRTNAKZIE-UHFFFAOYSA-N 2-(pentylamino)acetonitrile Chemical compound CCCCCNCC#N UYSWGJRTNAKZIE-UHFFFAOYSA-N 0.000 abstract 1
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 abstract 1
- WTUSXMPHNYCUBZ-UHFFFAOYSA-N C12(CC3CC(CC(C1)C3)C2)N(C(=O)Cl)CC Chemical compound C12(CC3CC(CC(C1)C3)C2)N(C(=O)Cl)CC WTUSXMPHNYCUBZ-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- PSZZQBYLCLZNNM-UHFFFAOYSA-N N-(1-adamantyl)-N-methylcarbamoyl chloride Chemical compound C12(CC3CC(CC(C1)C3)C2)N(C(=O)Cl)C PSZZQBYLCLZNNM-UHFFFAOYSA-N 0.000 abstract 1
- XTBOVDVHEUCPIF-UHFFFAOYSA-N N-(1-adamantyl)-N-octylcarbamoyl chloride Chemical compound C12(CC3CC(CC(C1)C3)C2)N(C(=O)Cl)CCCCCCCC XTBOVDVHEUCPIF-UHFFFAOYSA-N 0.000 abstract 1
- USDJGQLNFPZEON-UHFFFAOYSA-N [[4,6-bis(hydroxymethylamino)-1,3,5-triazin-2-yl]amino]methanol Chemical compound OCNC1=NC(NCO)=NC(NCO)=N1 USDJGQLNFPZEON-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 230000000840 anti-viral effect Effects 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 229940052761 dopaminergic adamantane derivative Drugs 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- PYZXUPBTKMMQGZ-UHFFFAOYSA-N ethyl 2-(octylamino)acetate Chemical compound CCCCCCCCNCC(=O)OCC PYZXUPBTKMMQGZ-UHFFFAOYSA-N 0.000 abstract 1
- KWTVXRPHUGEBNS-UHFFFAOYSA-N ethyl 2-(pentylamino)acetate Chemical compound CCCCCNCC(=O)OCC KWTVXRPHUGEBNS-UHFFFAOYSA-N 0.000 abstract 1
- OHGJZKDJUOSKEX-UHFFFAOYSA-N ethyl 2-[carbonochloridoyl(methyl)amino]acetate Chemical compound C(=O)(OCC)CN(C(=O)Cl)C OHGJZKDJUOSKEX-UHFFFAOYSA-N 0.000 abstract 1
- VMVZGGPZNHFGKS-UHFFFAOYSA-N ethyl n-(oxomethylidene)carbamate Chemical compound CCOC(=O)N=C=O VMVZGGPZNHFGKS-UHFFFAOYSA-N 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 239000012948 isocyanate Substances 0.000 abstract 1
- WZWKEEOAUZXNJJ-UHFFFAOYSA-N isocyanato acetate Chemical compound CC(=O)ON=C=O WZWKEEOAUZXNJJ-UHFFFAOYSA-N 0.000 abstract 1
- IRGXQOZJQZYLCT-UHFFFAOYSA-N n-(1-adamantyl)octanamide Chemical compound C1C(C2)CC3CC2CC1(NC(=O)CCCCCCC)C3 IRGXQOZJQZYLCT-UHFFFAOYSA-N 0.000 abstract 1
- FZAIZZSFCIYGIL-UHFFFAOYSA-N n-octyladamantan-1-amine Chemical compound C1C(C2)CC3CC2CC1(NCCCCCCCC)C3 FZAIZZSFCIYGIL-UHFFFAOYSA-N 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000005936 piperidyl group Chemical group 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C265/00—Derivatives of isocyanic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US87408469A | 1969-10-28 | 1969-10-28 | |
| US6915070A | 1970-09-02 | 1970-09-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1287317A true GB1287317A (en) | 1972-08-31 |
Family
ID=26749738
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5049070A Expired GB1287317A (en) | 1969-10-28 | 1970-10-23 | Novel adamantylurea derivatives and a process for the preparation thereof |
Country Status (9)
| Country | Link |
|---|---|
| AT (1) | AT302348B (enrdf_load_stackoverflow) |
| BE (1) | BE758165A (enrdf_load_stackoverflow) |
| CH (1) | CH543487A (enrdf_load_stackoverflow) |
| DE (1) | DE2052256A1 (enrdf_load_stackoverflow) |
| ES (1) | ES384946A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2070171B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1287317A (enrdf_load_stackoverflow) |
| NL (1) | NL7015825A (enrdf_load_stackoverflow) |
| SE (1) | SE356044B (enrdf_load_stackoverflow) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20090326039A1 (en) * | 2003-04-03 | 2009-12-31 | The Regents Of The University Of California | Inhibitors for the soluble epoxide hydrolase |
| WO2010112946A1 (en) | 2009-03-31 | 2010-10-07 | Rudjer Boskovic Institute | Adamantane bisurea derivatives, method of preparation and application in anion sensing |
| US8513302B2 (en) | 2003-04-03 | 2013-08-20 | The Regents Of The University Of California | Reducing nephropathy with inhibitors of soluble epoxide hydrolase and epoxyeicosanoids |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU767098B2 (en) * | 1998-03-26 | 2003-10-30 | University Of Saskatchewan | Aliphatic amino carboxylic and amino phosphonic acids, amino nitriles and amino tetrazoles as cellular rescue agents |
| US6984754B1 (en) | 1998-03-26 | 2006-01-10 | University Of Saskatchewan Technologies Inc. | Aliphatic amino carboxylic and amino phosphonic acids amino nitriles and amino tetrazoles as cellular rescue agents |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH456570A (de) * | 1965-11-18 | 1968-07-31 | Geigy Ag J R | Verfahren zur Herstellung von neuen substituierten Harnstoffderivaten |
-
0
- BE BE758165D patent/BE758165A/xx unknown
-
1970
- 1970-10-20 CH CH1551570A patent/CH543487A/de not_active IP Right Cessation
- 1970-10-21 SE SE1417970A patent/SE356044B/xx unknown
- 1970-10-23 GB GB5049070A patent/GB1287317A/en not_active Expired
- 1970-10-24 DE DE19702052256 patent/DE2052256A1/de active Pending
- 1970-10-27 FR FR7038744A patent/FR2070171B1/fr not_active Expired
- 1970-10-27 ES ES384946A patent/ES384946A1/es not_active Expired
- 1970-10-28 AT AT969670A patent/AT302348B/de not_active IP Right Cessation
- 1970-10-28 NL NL7015825A patent/NL7015825A/xx unknown
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20090326039A1 (en) * | 2003-04-03 | 2009-12-31 | The Regents Of The University Of California | Inhibitors for the soluble epoxide hydrolase |
| US8455652B2 (en) * | 2003-04-03 | 2013-06-04 | The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services | Inhibitors for the soluble epoxide hydrolase |
| US8513302B2 (en) | 2003-04-03 | 2013-08-20 | The Regents Of The University Of California | Reducing nephropathy with inhibitors of soluble epoxide hydrolase and epoxyeicosanoids |
| WO2010112946A1 (en) | 2009-03-31 | 2010-10-07 | Rudjer Boskovic Institute | Adamantane bisurea derivatives, method of preparation and application in anion sensing |
Also Published As
| Publication number | Publication date |
|---|---|
| AT302348B (de) | 1972-10-10 |
| FR2070171B1 (enrdf_load_stackoverflow) | 1975-04-18 |
| BE758165A (fr) | 1971-04-28 |
| CH543487A (de) | 1973-10-31 |
| DE2052256A1 (de) | 1971-05-06 |
| SE356044B (enrdf_load_stackoverflow) | 1973-05-14 |
| ES384946A1 (es) | 1973-09-01 |
| NL7015825A (enrdf_load_stackoverflow) | 1971-05-03 |
| FR2070171A1 (enrdf_load_stackoverflow) | 1971-09-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |