GB1351754A - Indenopyrrole derivatives - Google Patents
Indenopyrrole derivativesInfo
- Publication number
- GB1351754A GB1351754A GB3212070A GB1351754DA GB1351754A GB 1351754 A GB1351754 A GB 1351754A GB 3212070 A GB3212070 A GB 3212070A GB 1351754D A GB1351754D A GB 1351754DA GB 1351754 A GB1351754 A GB 1351754A
- Authority
- GB
- United Kingdom
- Prior art keywords
- pyrrol
- reacting
- benzyl
- oxo
- alkyl
- 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
- CNAFOLPGHNAMBW-UHFFFAOYSA-N indeno[2,1-b]pyrrole Chemical class C1=CC=CC2=CC3=NC=CC3=C21 CNAFOLPGHNAMBW-UHFFFAOYSA-N 0.000 title abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 6
- 150000001875 compounds Chemical class 0.000 abstract 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- SOHVBHRLBOMHIS-UHFFFAOYSA-N 2-(3-oxo-1,2-dihydroinden-1-yl)acetic acid Chemical class C1=CC=C2C(CC(=O)O)CC(=O)C2=C1 SOHVBHRLBOMHIS-UHFFFAOYSA-N 0.000 abstract 2
- QPYDOQHNDBUQHO-UHFFFAOYSA-N 3-benzyl-7-methoxy-3a,8b-dihydro-1H-indeno[2,3-b]pyrrole-2,4-dione Chemical compound C(C1=CC=CC=C1)N1C2C(CC1=O)C=1C=C(C=CC1C2=O)OC QPYDOQHNDBUQHO-UHFFFAOYSA-N 0.000 abstract 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 abstract 2
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 abstract 2
- 150000003951 lactams Chemical class 0.000 abstract 2
- 150000004702 methyl esters Chemical class 0.000 abstract 2
- 231100000252 nontoxic Toxicity 0.000 abstract 2
- 230000003000 nontoxic effect Effects 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 abstract 1
- TZLWTZIMIVMOSS-UHFFFAOYSA-N 2-(3-oxoinden-1-yl)acetic acid Chemical class O=C1C=C(C2=CC=CC=C12)CC(=O)O TZLWTZIMIVMOSS-UHFFFAOYSA-N 0.000 abstract 1
- NSQJISUSJNUSRW-UHFFFAOYSA-N 2-amino-6-methoxy-2,3-dihydroinden-1-one;hydrochloride Chemical compound Cl.COC1=CC=C2CC(N)C(=O)C2=C1 NSQJISUSJNUSRW-UHFFFAOYSA-N 0.000 abstract 1
- YCGJOSTWPJNHIU-UHFFFAOYSA-N 3-benzyl-7-methoxy-4-methyl-1,3a,4,8b-tetrahydroindeno[2,1-b]pyrrol-2-one Chemical compound C(C1=CC=CC=C1)N1C2C(CC1=O)C=1C=C(C=CC1C2C)OC YCGJOSTWPJNHIU-UHFFFAOYSA-N 0.000 abstract 1
- AETFDGBMVXAKNQ-UHFFFAOYSA-N 7-methoxy-1,3,3a,8b-tetrahydroindeno[2,3-b]pyrrole-2,4-dione Chemical compound COC=1C=CC=2C(C3NC(CC3C2C1)=O)=O AETFDGBMVXAKNQ-UHFFFAOYSA-N 0.000 abstract 1
- PBFNFXSZNPBSIU-UHFFFAOYSA-N 7-methoxy-2-methyl-3,4-dihydroindeno[2,1-b]pyrrole Chemical compound COC=1C=CC=2CC=3NC(=CC3C2C1)C PBFNFXSZNPBSIU-UHFFFAOYSA-N 0.000 abstract 1
- ROYATOXZXMBYJM-UHFFFAOYSA-N 7-methoxy-2-methyl-3,4-dihydroindeno[2,1-b]pyrrole-1-carboxylic acid Chemical compound COC=1C=CC=2CC=3NC(=C(C3C2C1)C(=O)O)C ROYATOXZXMBYJM-UHFFFAOYSA-N 0.000 abstract 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 1
- 229910019142 PO4 Inorganic materials 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 229960003116 amyl nitrite Drugs 0.000 abstract 1
- 230000000202 analgesic effect Effects 0.000 abstract 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 230000000911 decarboxylating effect Effects 0.000 abstract 1
- 238000006114 decarboxylation reaction Methods 0.000 abstract 1
- 125000005117 dialkylcarbamoyl group Chemical group 0.000 abstract 1
- LXCYSACZTOKNNS-UHFFFAOYSA-N diethoxy(oxo)phosphanium Chemical compound CCO[P+](=O)OCC LXCYSACZTOKNNS-UHFFFAOYSA-N 0.000 abstract 1
- ISOLMABRZPQKOV-UHFFFAOYSA-N diethyl 2-acetamidopropanedioate Chemical compound CCOC(=O)C(NC(C)=O)C(=O)OCC ISOLMABRZPQKOV-UHFFFAOYSA-N 0.000 abstract 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- UPOMPRQKAGEXPN-UHFFFAOYSA-N ethyl 3-(3-methoxyphenyl)prop-2-enoate Chemical compound CCOC(=O)C=CC1=CC=CC(OC)=C1 UPOMPRQKAGEXPN-UHFFFAOYSA-N 0.000 abstract 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 abstract 1
- 125000004494 ethyl ester group Chemical group 0.000 abstract 1
- 150000002311 glutaric acids Chemical class 0.000 abstract 1
- VANNPISTIUFMLH-UHFFFAOYSA-N glutaric anhydride Chemical compound O=C1CCCC(=O)O1 VANNPISTIUFMLH-UHFFFAOYSA-N 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- CSDTZUBPSYWZDX-UHFFFAOYSA-N n-pentyl nitrite Chemical compound CCCCCON=O CSDTZUBPSYWZDX-UHFFFAOYSA-N 0.000 abstract 1
- 125000004043 oxo group Chemical group O=* 0.000 abstract 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 abstract 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 abstract 1
- 239000010452 phosphate Substances 0.000 abstract 1
- 229920000137 polyphosphoric acid Polymers 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 238000007363 ring formation reaction Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/58—[b]- or [c]-condensed
- C07D209/70—[b]- or [c]-condensed containing carbocyclic rings other than six-membered
-
- 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
- C07D207/18—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 one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—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 one double bond between ring members or between a ring member and a non-ring member 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
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/273—2-Pyrrolidones 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 other ring carbon atoms
- C07D207/277—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D207/28—2-Pyrrolidone-5- carboxylic acids; Functional derivatives thereof, e.g. esters, nitriles
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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB3212070 | 1970-07-02 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1351754A true GB1351754A (en) | 1974-05-01 |
Family
ID=10333570
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB3212070A Expired GB1351754A (en) | 1970-07-02 | 1970-07-02 | Indenopyrrole derivatives |
Country Status (12)
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2740562A1 (de) * | 1976-09-15 | 1978-03-23 | American Cyanamid Co | Optisch aktive azabicyclohexane, verfahren zu ihrer herstellung und sie enthaltende arzneimittel |
JPH0720933B2 (ja) * | 1990-07-12 | 1995-03-08 | ファイザー・インコーポレーテッド | インダノピロリジンカルバメート |
CN102381961A (zh) * | 2011-09-03 | 2012-03-21 | 四川大学 | 3-苯基戊二酸类化合物、其制备方法和用途 |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3878225A (en) * | 1973-03-01 | 1975-04-15 | Hoechst Co American | Condensed pyrroles bearing an N-phenyl substituent |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1277789A (en) * | 1969-09-08 | 1972-06-14 | Logeais Labor Jacques | Improvements in or relating to new polycyclic pyrrole derivatives |
-
1970
- 1970-07-02 GB GB3212070A patent/GB1351754A/en not_active Expired
-
1971
- 1971-06-24 ZA ZA714137A patent/ZA714137B/xx unknown
- 1971-06-24 CA CA116,503A patent/CA948206A/en not_active Expired
- 1971-06-24 IL IL37146A patent/IL37146A/xx unknown
- 1971-06-30 BE BE769303A patent/BE769303A/xx unknown
- 1971-07-01 AT AT570671A patent/AT305996B/de not_active IP Right Cessation
- 1971-07-01 SE SE7108558A patent/SE377117B/xx unknown
- 1971-07-01 AT AT307772A patent/AT310731B/de not_active IP Right Cessation
- 1971-07-01 FR FR7124127A patent/FR2100854B1/fr not_active Expired
- 1971-07-01 DE DE19712132810 patent/DE2132810A1/de active Pending
- 1971-07-02 ES ES392848A patent/ES392848A1/es not_active Expired
- 1971-07-02 CH CH978671A patent/CH570980A5/xx not_active IP Right Cessation
- 1971-07-02 NL NL7109212A patent/NL7109212A/xx unknown
-
1973
- 1973-10-05 ES ES419386A patent/ES419386A1/es not_active Expired
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2740562A1 (de) * | 1976-09-15 | 1978-03-23 | American Cyanamid Co | Optisch aktive azabicyclohexane, verfahren zu ihrer herstellung und sie enthaltende arzneimittel |
JPH0720933B2 (ja) * | 1990-07-12 | 1995-03-08 | ファイザー・インコーポレーテッド | インダノピロリジンカルバメート |
CN102381961A (zh) * | 2011-09-03 | 2012-03-21 | 四川大学 | 3-苯基戊二酸类化合物、其制备方法和用途 |
CN102381961B (zh) * | 2011-09-03 | 2014-01-15 | 四川大学 | 3-苯基戊二酸类化合物、其制备方法和用途 |
Also Published As
Publication number | Publication date |
---|---|
AT310731B (de) | 1973-10-10 |
BE769303A (fr) | 1971-12-30 |
FR2100854A1 (enrdf_load_stackoverflow) | 1972-03-24 |
AT305996B (de) | 1973-03-26 |
IL37146A (en) | 1974-10-22 |
CA948206A (en) | 1974-05-28 |
CH570980A5 (enrdf_load_stackoverflow) | 1975-12-31 |
ES419386A1 (es) | 1976-07-01 |
ES392848A1 (es) | 1974-07-16 |
SE377117B (enrdf_load_stackoverflow) | 1975-06-23 |
NL7109212A (enrdf_load_stackoverflow) | 1972-01-04 |
ZA714137B (en) | 1972-03-29 |
DE2132810A1 (de) | 1972-01-05 |
IL37146A0 (en) | 1971-08-25 |
FR2100854B1 (enrdf_load_stackoverflow) | 1974-11-15 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
414F | Notice of opposition given (sect. 14/1949) | ||
414A | Case decided by the comptroller ** specification amended (sect. 14/1949) | ||
4145 | Application made to the patents appeal tribunal (sect. 14/1949) | ||
4140 | Case decided on appeal ** appeal allowed in part (sect. 14/1949) | ||
414A | Case decided by the comptroller ** specification amended (sect. 14/1949) | ||
SPA | Amended specification published | ||
PS | Patent sealed [section 19, patents act 1949] | ||
PCNP | Patent ceased through non-payment of renewal fee |