GB1204804A - A process for the preparation of pyrroline derivatives - Google Patents
A process for the preparation of pyrroline derivativesInfo
- Publication number
- GB1204804A GB1204804A GB56314/69A GB5631469A GB1204804A GB 1204804 A GB1204804 A GB 1204804A GB 56314/69 A GB56314/69 A GB 56314/69A GB 5631469 A GB5631469 A GB 5631469A GB 1204804 A GB1204804 A GB 1204804A
- Authority
- GB
- United Kingdom
- Prior art keywords
- diphenyl
- cyano
- acid
- dimethyl
- isocyanate
- 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
- 150000003236 pyrrolines Chemical class 0.000 title abstract 3
- 150000001408 amides Chemical class 0.000 abstract 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 125000005036 alkoxyphenyl group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000005037 alkyl phenyl group Chemical group 0.000 abstract 2
- 235000010290 biphenyl Nutrition 0.000 abstract 2
- 239000004305 biphenyl Substances 0.000 abstract 2
- 239000003153 chemical reaction reagent Substances 0.000 abstract 2
- 239000003638 chemical reducing agent Substances 0.000 abstract 2
- 125000005059 halophenyl group Chemical group 0.000 abstract 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- DWMCGBDXDISIQW-UHFFFAOYSA-N 2-(2-cyano-2,2-diphenylethyl)-4-methylpentanoic acid Chemical compound C(C(C)C)C(C(=O)O)CC(C1=CC=CC=C1)(C1=CC=CC=C1)C#N DWMCGBDXDISIQW-UHFFFAOYSA-N 0.000 abstract 1
- DRCAXKMNVXYVBE-UHFFFAOYSA-N 2-(2-cyano-2,2-diphenylethyl)hexanoic acid Chemical compound C(CCC)C(C(=O)O)CC(C1=CC=CC=C1)(C1=CC=CC=C1)C#N DRCAXKMNVXYVBE-UHFFFAOYSA-N 0.000 abstract 1
- COIOSINGXCQTFP-UHFFFAOYSA-N 2-(2-cyano-2,2-diphenylethyl)octanoic acid Chemical compound C(CCCCC)C(C(=O)O)CC(C1=CC=CC=C1)(C1=CC=CC=C1)C#N COIOSINGXCQTFP-UHFFFAOYSA-N 0.000 abstract 1
- CHIXVGJEMMFOJV-UHFFFAOYSA-N 2-[cyano(diphenyl)methyl]hexanoic acid Chemical compound C(#N)C(C(C(=O)O)CCCC)(C1=CC=CC=C1)C1=CC=CC=C1 CHIXVGJEMMFOJV-UHFFFAOYSA-N 0.000 abstract 1
- -1 2-amino-3,3-diphenyl-4- butyl- Chemical group 0.000 abstract 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 abstract 1
- SXJBNDCFYYBLHB-UHFFFAOYSA-N 3-cyano-2,2-dimethyl-3,3-diphenylpropanoyl chloride Chemical compound CC(C(=O)Cl)(C(C#N)(C1=CC=CC=C1)C1=CC=CC=C1)C SXJBNDCFYYBLHB-UHFFFAOYSA-N 0.000 abstract 1
- BRFWTAKQNHABCH-UHFFFAOYSA-N 3-cyano-2-methyl-3,3-diphenylpropanoyl chloride Chemical compound C=1C=CC=CC=1C(C#N)(C(C(Cl)=O)C)C1=CC=CC=C1 BRFWTAKQNHABCH-UHFFFAOYSA-N 0.000 abstract 1
- VWFADTMXOCQDRW-UHFFFAOYSA-N 4-bromo-2-(4-methylphenyl)-2-phenylbutanenitrile Chemical compound C1=CC(C)=CC=C1C(CCBr)(C#N)C1=CC=CC=C1 VWFADTMXOCQDRW-UHFFFAOYSA-N 0.000 abstract 1
- PHIYBMUVAJLSGS-UHFFFAOYSA-N 4-cyano-2-ethyl-4,4-diphenylbutanoic acid Chemical compound C=1C=CC=CC=1C(C#N)(CC(CC)C(O)=O)C1=CC=CC=C1 PHIYBMUVAJLSGS-UHFFFAOYSA-N 0.000 abstract 1
- KXTWEMMHVYVLBZ-UHFFFAOYSA-N 4-isocyanato-2,2-diphenyldecanenitrile Chemical compound C1(=CC=CC=C1)C(CC(CCCCCC)N=C=O)(C#N)C1=CC=CC=C1 KXTWEMMHVYVLBZ-UHFFFAOYSA-N 0.000 abstract 1
- QKKIJRBIKSWVBQ-UHFFFAOYSA-N 4-isocyanato-2,2-diphenylhexanenitrile Chemical compound C1(=CC=CC=C1)C(CC(CC)N=C=O)(C#N)C1=CC=CC=C1 QKKIJRBIKSWVBQ-UHFFFAOYSA-N 0.000 abstract 1
- XNNNPJPAKICHCM-UHFFFAOYSA-N 4-isocyanato-2,2-diphenyloctanenitrile Chemical compound C1(=CC=CC=C1)C(CC(CCCC)N=C=O)(C#N)C1=CC=CC=C1 XNNNPJPAKICHCM-UHFFFAOYSA-N 0.000 abstract 1
- IBMCRFACMDNJPX-UHFFFAOYSA-N 4-isocyanato-6-methyl-2,2-diphenylheptanenitrile Chemical compound C1(=CC=CC=C1)C(CC(CC(C)C)N=C=O)(C#N)C1=CC=CC=C1 IBMCRFACMDNJPX-UHFFFAOYSA-N 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000000392 cycloalkenyl group Chemical group 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- RTGMBNOVQREPEA-UHFFFAOYSA-N dimethyl 2-(2-cyano-2,2-diphenylethyl)-2-ethylpropanedioate Chemical compound C(C)C(C(=O)OC)(C(=O)OC)CC(C#N)(C1=CC=CC=C1)C1=CC=CC=C1 RTGMBNOVQREPEA-UHFFFAOYSA-N 0.000 abstract 1
- WDUVRNYDOSBRSU-UHFFFAOYSA-N dimethyl 2-[(dimethylamino)methyl]-2-ethylpropanedioate hydrochloride Chemical compound Cl.COC(C(C(=O)OC)(CC)CN(C)C)=O WDUVRNYDOSBRSU-UHFFFAOYSA-N 0.000 abstract 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- ABWRYMJFLCUBMZ-UHFFFAOYSA-N ethyl 2-(2-cyano-2,2-diphenylethyl)hexanoate Chemical compound C(CCC)C(C(=O)OCC)CC(C1=CC=CC=C1)(C1=CC=CC=C1)C#N ABWRYMJFLCUBMZ-UHFFFAOYSA-N 0.000 abstract 1
- ZONYXWQDUYMKFB-UHFFFAOYSA-N flavanone Chemical compound O1C2=CC=CC=C2C(=O)CC1C1=CC=CC=C1 ZONYXWQDUYMKFB-UHFFFAOYSA-N 0.000 abstract 1
- 239000012458 free base Substances 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
- 150000002513 isocyanates Chemical class 0.000 abstract 1
- LUPGIKWTNNINKA-UHFFFAOYSA-N methyl 2-[cyano(diphenyl)methyl]hexanoate Chemical compound C(#N)C(C(C(=O)OC)CCCC)(C1=CC=CC=C1)C1=CC=CC=C1 LUPGIKWTNNINKA-UHFFFAOYSA-N 0.000 abstract 1
- ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 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
- C07D207/18—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
-
- 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
- C07D207/34—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 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
- C07D207/36—Oxygen or sulfur atoms
- C07D207/38—2-Pyrrolones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH290567A CH501615A (de) | 1967-02-27 | 1967-02-27 | Verfahren zur Herstellung von Pyrrolidinverbindungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1204804A true GB1204804A (en) | 1970-09-09 |
Family
ID=4244242
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB56314/69A Expired GB1204804A (en) | 1967-02-27 | 1968-02-26 | A process for the preparation of pyrroline derivatives |
| GB9202/68A Expired GB1204803A (en) | 1967-02-27 | 1968-02-26 | Novel pyrroline derivatives and a process for the manufacture thereof |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB9202/68A Expired GB1204803A (en) | 1967-02-27 | 1968-02-26 | Novel pyrroline derivatives and a process for the manufacture thereof |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3564010A (OSRAM) |
| AT (2) | AT283341B (OSRAM) |
| BE (1) | BE711260A (OSRAM) |
| CH (7) | CH514584A (OSRAM) |
| DE (1) | DE1695220C3 (OSRAM) |
| ES (1) | ES350956A1 (OSRAM) |
| FR (2) | FR8382M (OSRAM) |
| GB (2) | GB1204804A (OSRAM) |
| IE (1) | IE31968B1 (OSRAM) |
| IL (2) | IL37775A (OSRAM) |
| NL (1) | NL6802460A (OSRAM) |
| NO (1) | NO125927B (OSRAM) |
| SE (2) | SE331996B (OSRAM) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4005100A (en) * | 1972-02-28 | 1977-01-25 | Hoffmann-La Roche Inc. | Pyrazole-5-carboxamides |
| CA1201119A (en) * | 1978-09-18 | 1986-02-25 | Mcneilab, Inc. | Diaza-cyclic derivatives of guanidine |
| EP0020304A1 (de) * | 1979-05-29 | 1980-12-10 | Ciba-Geigy Ag | Guanidine, Verfahren zur Herstellung, pharmazeutische Präparate enthaltend solche Verbindungen und ihre Verwendung |
| JPS55160764A (en) * | 1979-05-29 | 1980-12-13 | Ciba Geigy Ag | Guanidine* its manufacture and pharmaceutic medicine containing same |
-
1967
- 1967-02-27 CH CH1791169A patent/CH514584A/de not_active IP Right Cessation
- 1967-02-27 CH CH290567A patent/CH501615A/de not_active IP Right Cessation
- 1967-02-27 CH CH1791369A patent/CH513849A/de not_active IP Right Cessation
- 1967-02-27 CH CH1791069A patent/CH513158A/de not_active IP Right Cessation
- 1967-02-27 CH CH1790869A patent/CH513156A/de not_active IP Right Cessation
- 1967-02-27 CH CH1791469A patent/CH513850A/de not_active IP Right Cessation
- 1967-02-27 CH CH1791269A patent/CH513848A/de not_active IP Right Cessation
-
1968
- 1968-01-16 AT AT04284/69A patent/AT283341B/de active
- 1968-01-16 DE DE1695220A patent/DE1695220C3/de not_active Expired
- 1968-01-16 AT AT42968A patent/AT277222B/de not_active IP Right Cessation
- 1968-02-18 IL IL37775A patent/IL37775A/xx unknown
- 1968-02-18 IL IL29491A patent/IL29491A/en unknown
- 1968-02-20 FR FR140496A patent/FR8382M/fr not_active Expired
- 1968-02-21 NL NL6802460A patent/NL6802460A/xx unknown
- 1968-02-23 US US707484A patent/US3564010A/en not_active Expired - Lifetime
- 1968-02-26 ES ES350956A patent/ES350956A1/es not_active Expired
- 1968-02-26 GB GB56314/69A patent/GB1204804A/en not_active Expired
- 1968-02-26 NO NO0699/68A patent/NO125927B/no unknown
- 1968-02-26 BE BE711260D patent/BE711260A/xx unknown
- 1968-02-26 GB GB9202/68A patent/GB1204803A/en not_active Expired
- 1968-02-26 SE SE02451/68A patent/SE331996B/xx unknown
- 1968-02-27 IE IE230/68A patent/IE31968B1/xx unknown
- 1968-02-27 FR FR141415A patent/FR1573948A/fr not_active Expired
- 1968-08-27 SE SE11504/68A patent/SE340620B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR8382M (OSRAM) | 1971-03-01 |
| CH513848A (de) | 1971-10-15 |
| CH513849A (de) | 1971-10-15 |
| SE340620B (OSRAM) | 1971-11-29 |
| IL37775A (en) | 1972-01-27 |
| IL29491A (en) | 1972-01-27 |
| CH501615A (de) | 1971-01-15 |
| IE31968L (en) | 1968-08-27 |
| IE31968B1 (en) | 1973-03-07 |
| BE711260A (OSRAM) | 1968-08-26 |
| NO125927B (OSRAM) | 1972-11-27 |
| CH513156A (de) | 1971-09-30 |
| GB1204803A (en) | 1970-09-09 |
| DE1695220B2 (de) | 1980-01-10 |
| CH514584A (de) | 1971-10-31 |
| NL6802460A (OSRAM) | 1968-08-28 |
| AT283341B (de) | 1970-08-10 |
| CH513850A (de) | 1971-10-15 |
| CH513158A (de) | 1971-09-30 |
| ES350956A1 (es) | 1969-05-16 |
| AT277222B (de) | 1969-12-10 |
| US3564010A (en) | 1971-02-16 |
| DE1695220A1 (de) | 1971-03-18 |
| FR1573948A (OSRAM) | 1969-07-11 |
| DE1695220C3 (de) | 1980-09-11 |
| SE331996B (OSRAM) | 1971-01-25 |
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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 |