GB1334070A - Tris- and tetrakis- 1,2,3,4-tetrahydroisoquinoline and -3,4- dihydroisoquinoline compounds - Google Patents
Tris- and tetrakis- 1,2,3,4-tetrahydroisoquinoline and -3,4- dihydroisoquinoline compoundsInfo
- Publication number
- GB1334070A GB1334070A GB6184170A GB6184170A GB1334070A GB 1334070 A GB1334070 A GB 1334070A GB 6184170 A GB6184170 A GB 6184170A GB 6184170 A GB6184170 A GB 6184170A GB 1334070 A GB1334070 A GB 1334070A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- groups
- ethyl
- oxo
- substituents
- 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
- UWYZHKAOTLEWKK-UHFFFAOYSA-N tetrahydro-isoquinoline Natural products C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 title abstract 3
- 239000002253 acid Substances 0.000 abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 5
- 125000001424 substituent group Chemical group 0.000 abstract 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 abstract 3
- 125000003545 alkoxy group Chemical group 0.000 abstract 3
- 230000007062 hydrolysis Effects 0.000 abstract 3
- 238000006460 hydrolysis reaction Methods 0.000 abstract 3
- 238000007142 ring opening reaction Methods 0.000 abstract 3
- -1 tetracarboxylic acid ester Chemical class 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
- POROIMOHDIEBBO-UHFFFAOYSA-N 2-oxocyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1=O POROIMOHDIEBBO-UHFFFAOYSA-N 0.000 abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical class NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 abstract 2
- 125000005530 alkylenedioxy group Chemical group 0.000 abstract 2
- 150000001408 amides Chemical class 0.000 abstract 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 150000004702 methyl esters Chemical class 0.000 abstract 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 abstract 2
- 150000003628 tricarboxylic acids Chemical class 0.000 abstract 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 abstract 1
- IOEPOEDBBPRAEI-UHFFFAOYSA-N 1,2-dihydroisoquinoline Chemical group C1=CC=C2CNC=CC2=C1 IOEPOEDBBPRAEI-UHFFFAOYSA-N 0.000 abstract 1
- VEFLKXRACNJHOV-UHFFFAOYSA-N 1,3-dibromopropane Chemical compound BrCCCBr VEFLKXRACNJHOV-UHFFFAOYSA-N 0.000 abstract 1
- ULTHEAFYOOPTTB-UHFFFAOYSA-N 1,4-dibromobutane Chemical compound BrCCCCBr ULTHEAFYOOPTTB-UHFFFAOYSA-N 0.000 abstract 1
- FXBPINRBSNMESY-UHFFFAOYSA-N 2-oxocyclopentane-1-carboxylic acid Chemical compound OC(=O)C1CCCC1=O FXBPINRBSNMESY-UHFFFAOYSA-N 0.000 abstract 1
- NKSZCPBUWGZONP-UHFFFAOYSA-N 3,4-dihydroisoquinoline Chemical class C1=CC=C2C=NCCC2=C1 NKSZCPBUWGZONP-UHFFFAOYSA-N 0.000 abstract 1
- IJTHHRNQGWVNDV-UHFFFAOYSA-N 4-(2-carboxyethyl)-4-(4-chlorobenzoyl)heptanedioic acid Chemical compound OC(=O)CCC(CCC(O)=O)(CCC(O)=O)C(=O)C1=CC=C(Cl)C=C1 IJTHHRNQGWVNDV-UHFFFAOYSA-N 0.000 abstract 1
- YHRHPFBHYLVUEC-UHFFFAOYSA-N 4-bromo-2-ethylbut-2-enoic acid Chemical compound CCC(C(O)=O)=CCBr YHRHPFBHYLVUEC-UHFFFAOYSA-N 0.000 abstract 1
- GQPMGERAJYUBIV-UHFFFAOYSA-M C(C=O)(=S)[O-].[Na+] Chemical compound C(C=O)(=S)[O-].[Na+] GQPMGERAJYUBIV-UHFFFAOYSA-M 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- 208000007536 Thrombosis Diseases 0.000 abstract 1
- 239000007983 Tris buffer Substances 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 125000004104 aryloxy group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000002843 carboxylic acid group Chemical group 0.000 abstract 1
- 150000001805 chlorine compounds Chemical class 0.000 abstract 1
- 230000035602 clotting Effects 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 238000007278 cyanoethylation reaction Methods 0.000 abstract 1
- 238000006264 debenzylation reaction Methods 0.000 abstract 1
- 230000017858 demethylation Effects 0.000 abstract 1
- 238000010520 demethylation reaction Methods 0.000 abstract 1
- VKCMWLOBUILIOQ-UHFFFAOYSA-N ethyl 3-bromo-2-oxocyclohexane-1-carboxylate Chemical compound CCOC(=O)C1CCCC(Br)C1=O VKCMWLOBUILIOQ-UHFFFAOYSA-N 0.000 abstract 1
- 125000004494 ethyl ester group Chemical group 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- GXERADRSPIXCIF-UHFFFAOYSA-N o-ethyl 2-oxoethanethioate Chemical compound CCOC(=S)C=O GXERADRSPIXCIF-UHFFFAOYSA-N 0.000 abstract 1
- 125000000962 organic group Chemical group 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000000546 pharmaceutical excipient Substances 0.000 abstract 1
- 229940117803 phenethylamine Drugs 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 abstract 1
- 150000000000 tetracarboxylic acids Chemical class 0.000 abstract 1
- WWIKEXOUUOFLNY-UHFFFAOYSA-N tetraethyl undecane-1,4,8,11-tetracarboxylate Chemical compound C(CCC(CCCC(CCCC(=O)OCC)C(=O)OCC)C(=O)OCC)C(=O)OCC WWIKEXOUUOFLNY-UHFFFAOYSA-N 0.000 abstract 1
- WGVOSKVOSIYESH-UHFFFAOYSA-N tetramethyl tetradecane-1,5,10,14-tetracarboxylate Chemical compound COC(=O)CCCCC(C(=O)OC)CCCCC(C(=O)OC)CCCCC(=O)OC WGVOSKVOSIYESH-UHFFFAOYSA-N 0.000 abstract 1
- OVRJVKCZJCNSOW-UHFFFAOYSA-N thian-4-one Chemical compound O=C1CCSCC1 OVRJVKCZJCNSOW-UHFFFAOYSA-N 0.000 abstract 1
- DJMVDACSXNSXOJ-UHFFFAOYSA-N triethyl heptane-1,4,7-tricarboxylate Chemical compound CCOC(=O)CCCC(C(=O)OCC)CCCC(=O)OCC DJMVDACSXNSXOJ-UHFFFAOYSA-N 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/60—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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/235—Saturated compounds containing more than one carboxyl group
- C07C59/305—Saturated compounds containing more than one carboxyl group containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/88—Unsaturated compounds containing keto groups containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
- C07D217/16—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings 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
- C07D309/10—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/58—Radicals substituted by nitrogen atoms
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)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US102970A | 1970-01-06 | 1970-01-06 | |
| US16534671A | 1971-07-22 | 1971-07-22 | |
| US336973A US3928611A (en) | 1970-01-06 | 1973-03-01 | Tris- and tetrakis- (1,2,3,4-tetrahydroisoquinoline) and -{8 3,4-dihydroisoquinoline{9 {0 compounds in inhibiting and dissolving blood clots |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1334070A true GB1334070A (en) | 1973-10-17 |
Family
ID=27356801
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB6184170A Expired GB1334070A (en) | 1970-01-06 | 1970-12-30 | Tris- and tetrakis- 1,2,3,4-tetrahydroisoquinoline and -3,4- dihydroisoquinoline compounds |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3928611A (enExample) |
| BE (1) | BE761221A (enExample) |
| CA (1) | CA968802A (enExample) |
| CH (1) | CH550798A (enExample) |
| DE (1) | DE2100331A1 (enExample) |
| FR (1) | FR2081413B1 (enExample) |
| GB (1) | GB1334070A (enExample) |
| NL (1) | NL7100005A (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4107165A (en) * | 1970-01-06 | 1978-08-15 | Endo Laboratories | Tris[tetrahydroisoquinoline] compounds |
-
1970
- 1970-12-30 GB GB6184170A patent/GB1334070A/en not_active Expired
-
1971
- 1971-01-04 CA CA101,945A patent/CA968802A/en not_active Expired
- 1971-01-04 NL NL7100005A patent/NL7100005A/xx unknown
- 1971-01-05 CH CH8571A patent/CH550798A/xx not_active IP Right Cessation
- 1971-01-05 BE BE761221A patent/BE761221A/xx unknown
- 1971-01-06 FR FR7100182A patent/FR2081413B1/fr not_active Expired
- 1971-06-05 DE DE19712100331 patent/DE2100331A1/de active Pending
-
1973
- 1973-03-01 US US336973A patent/US3928611A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| FR2081413A1 (enExample) | 1971-12-03 |
| BE761221A (fr) | 1971-06-16 |
| CA968802A (en) | 1975-06-03 |
| US3928611A (en) | 1975-12-23 |
| NL7100005A (enExample) | 1971-07-08 |
| FR2081413B1 (enExample) | 1975-04-18 |
| CH550798A (de) | 1974-06-28 |
| DE2100331A1 (enExample) | 1971-07-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| IE43506L (en) | Isoquinolines | |
| SE7506327L (sv) | Forfarande for framstellning av 8-tiometylergoliner | |
| GB1446484A (en) | Penicillins their preparation and use | |
| GB1491510A (en) | 1-nitrophenylquinazoline-2,4(1h,3h)-diones | |
| GB1459065A (en) | Therapeutic thiophene derivatives | |
| GB1507717A (en) | Benz(de)isoquinoline derivatives | |
| GB1334070A (en) | Tris- and tetrakis- 1,2,3,4-tetrahydroisoquinoline and -3,4- dihydroisoquinoline compounds | |
| US3896166A (en) | Formyl-substituted tyrosine | |
| GB1515059A (en) | 3-aminomethylene-6,7-dimethoxy-2-methyl-4-oxo-1,2,3,4-tetrahydro-1-quinoline carboxylic acid esters | |
| KR910007884A (ko) | 이소퀴놀론 유도체, 그의 제조방법 및 용도 | |
| US3437662A (en) | Polyhydroisoquinoline antiviral agents | |
| GB1398800A (en) | Trisubstituted imidazoles | |
| US3647802A (en) | 2-amino-4-aryl-3 4-dihydroquinolines | |
| GB1273705A (en) | A method for producing 3,5-diaryl-4-pyrazole acetic acids | |
| GB1453417A (en) | Nitroimidazoles | |
| GB1470493A (en) | Anti-hypertensive 4-1-2-naphthyl-methyl-1,2,5,6-tetrahydro pyrid-4-yl-chroman-5-ol esters | |
| GB1367743A (en) | 2,4,5-trisubstituted oxazoles and pharmaceutical uses thereof | |
| GB1386664A (en) | Aminothiophene-carboxylic acid esters and process for their preparation | |
| GB1441184A (en) | Esters of 2- 4-quinolyl- amino- benzoic acids | |
| GB1511599A (en) | N-(4-benzamido)-2-pyrrolidone-4-carboxylic acids and derivatives thereof | |
| GB1128607A (en) | Indole derivatives | |
| GB1504683A (en) | Pharmaceutical compositions containing substituted pyrimido-quinoline derivatives | |
| GB1178187A (en) | Bis(tetrahydroisoquinolines) and compositions thereof | |
| GB1242096A (en) | Benzobenzofuranooxepine compounds and process for preparing the same | |
| US4107165A (en) | Tris[tetrahydroisoquinoline] compounds |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |