GB1390866A - Cycloalkanoyl-substituted pyrroles and pharmaceutical compo sitions containing them - Google Patents
Cycloalkanoyl-substituted pyrroles and pharmaceutical compo sitions containing themInfo
- Publication number
- GB1390866A GB1390866A GB285473A GB285473A GB1390866A GB 1390866 A GB1390866 A GB 1390866A GB 285473 A GB285473 A GB 285473A GB 285473 A GB285473 A GB 285473A GB 1390866 A GB1390866 A GB 1390866A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compound
- formula
- acetonitrile
- methylpyrrole
- expl
- 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
- 239000008194 pharmaceutical composition Chemical class 0.000 title abstract 2
- 150000003233 pyrroles Chemical class 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 15
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 238000006243 chemical reaction Methods 0.000 abstract 4
- ROSYAUHHRKAPHX-UHFFFAOYSA-N 2-(1-methylpyrrol-2-yl)acetonitrile Chemical compound CN1C=CC=C1CC#N ROSYAUHHRKAPHX-UHFFFAOYSA-N 0.000 abstract 2
- QVIPGTBUPIYKHZ-UHFFFAOYSA-N 2-[5-(cyclohexanecarbonyl)-1-methylpyrrol-2-yl]acetonitrile Chemical compound C1(CCCCC1)C(=O)C1=CC=C(N1C)CC#N QVIPGTBUPIYKHZ-UHFFFAOYSA-N 0.000 abstract 2
- RVOJTCZRIKWHDX-UHFFFAOYSA-N cyclohexanecarbonyl chloride Chemical compound ClC(=O)C1CCCCC1 RVOJTCZRIKWHDX-UHFFFAOYSA-N 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 238000007069 methylation reaction Methods 0.000 abstract 2
- 238000010561 standard procedure Methods 0.000 abstract 2
- MKVATVUOVMCHJJ-UHFFFAOYSA-N 2-(1h-pyrrol-2-yl)acetonitrile Chemical compound N#CCC1=CC=CN1 MKVATVUOVMCHJJ-UHFFFAOYSA-N 0.000 abstract 1
- MPSPUILUUKSWEM-UHFFFAOYSA-N 2-[3-(cyclohexanecarbonyl)-1H-pyrrol-2-yl]acetonitrile Chemical compound C1(CCCCC1)C(=O)C1=C(NC=C1)CC#N MPSPUILUUKSWEM-UHFFFAOYSA-N 0.000 abstract 1
- WJAFJPUFNBKJQO-UHFFFAOYSA-N 2-[5-(cyclohexanecarbonyl)-1-ethylpyrrol-2-yl]acetonitrile Chemical compound C1(CCCCC1)C(=O)C1=CC=C(N1CC)CC#N WJAFJPUFNBKJQO-UHFFFAOYSA-N 0.000 abstract 1
- AWCUYSVWZSDEGM-UHFFFAOYSA-N 2-[5-(cyclohexanecarbonyl)-1-methylpyrrol-2-yl]acetamide Chemical compound C1(CCCCC1)C(=O)C1=CC=C(N1C)CC(=O)N AWCUYSVWZSDEGM-UHFFFAOYSA-N 0.000 abstract 1
- YPBBZKSAEIPGKA-UHFFFAOYSA-N 2-[5-(cyclopentanecarbonyl)-1-methylpyrrol-2-yl]acetonitrile Chemical compound C1(CCCC1)C(=O)C1=CC=C(N1C)CC#N YPBBZKSAEIPGKA-UHFFFAOYSA-N 0.000 abstract 1
- VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 abstract 1
- -1 5 - cyclohexylcarbonyl Chemical group 0.000 abstract 1
- PFHKDTWSMUGJAS-UHFFFAOYSA-N C(=O)=C(C#N)C=1N(C=CC1)C Chemical compound C(=O)=C(C#N)C=1N(C=CC1)C PFHKDTWSMUGJAS-UHFFFAOYSA-N 0.000 abstract 1
- NMMVELBWVSYQOJ-UHFFFAOYSA-N CN1C(=CC=C1C(CC1=CC=CC=C1)=O)CC#N Chemical compound CN1C(=CC=C1C(CC1=CC=CC=C1)=O)CC#N NMMVELBWVSYQOJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000002841 Lewis acid Substances 0.000 abstract 1
- 238000007126 N-alkylation reaction Methods 0.000 abstract 1
- 239000004480 active ingredient Substances 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
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 239000003701 inert diluent Substances 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 150000007517 lewis acids Chemical class 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/337—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrrole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US00219861A US3803169A (en) | 1972-01-21 | 1972-01-21 | Cycloalkanoyl-substituted pyrroles |
| US00219864A US3803171A (en) | 1972-01-21 | 1972-01-21 | 5-phenylacetyl-pyrroles |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1390866A true GB1390866A (en) | 1975-04-16 |
Family
ID=26914338
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB285473A Expired GB1390866A (en) | 1972-01-21 | 1973-01-19 | Cycloalkanoyl-substituted pyrroles and pharmaceutical compo sitions containing them |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS4880556A (cs) |
| AT (1) | AT326115B (cs) |
| BE (1) | BE794160A (cs) |
| CA (1) | CA996939A (cs) |
| CH (1) | CH587815A5 (cs) |
| DE (1) | DE2302671A1 (cs) |
| FR (1) | FR2183658B1 (cs) |
| GB (1) | GB1390866A (cs) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996010013A1 (en) * | 1994-09-27 | 1996-04-04 | Ono Pharmaceutical Co., Ltd. | Five membered heterocyclic compounds |
| US5859042A (en) * | 1995-09-27 | 1999-01-12 | Ono Pharmaceutical Co., Ltd. | Five membered heterocyclic compounds |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0023938B1 (en) * | 1979-08-13 | 1983-07-20 | McNeilab, Inc. | Preparation of pyrrole-2-acetates |
-
0
- BE BE794160D patent/BE794160A/xx unknown
-
1973
- 1973-01-18 FR FR7301764A patent/FR2183658B1/fr not_active Expired
- 1973-01-19 CH CH82473A patent/CH587815A5/xx not_active IP Right Cessation
- 1973-01-19 AT AT47373A patent/AT326115B/de not_active IP Right Cessation
- 1973-01-19 GB GB285473A patent/GB1390866A/en not_active Expired
- 1973-01-19 DE DE19732302671 patent/DE2302671A1/de active Pending
- 1973-01-19 CA CA161,656A patent/CA996939A/en not_active Expired
- 1973-01-22 JP JP940073A patent/JPS4880556A/ja active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996010013A1 (en) * | 1994-09-27 | 1996-04-04 | Ono Pharmaceutical Co., Ltd. | Five membered heterocyclic compounds |
| US5859042A (en) * | 1995-09-27 | 1999-01-12 | Ono Pharmaceutical Co., Ltd. | Five membered heterocyclic compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2183658A1 (cs) | 1973-12-21 |
| CH587815A5 (cs) | 1977-05-13 |
| BE794160A (fr) | 1973-07-17 |
| JPS4880556A (cs) | 1973-10-29 |
| ATA47373A (de) | 1975-02-15 |
| FR2183658B1 (cs) | 1975-11-21 |
| CA996939A (en) | 1976-09-14 |
| DE2302671A1 (de) | 1973-07-26 |
| AT326115B (de) | 1975-11-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |