GB991838A - Quinoline derivatives - Google Patents
Quinoline derivativesInfo
- Publication number
- GB991838A GB991838A GB23888/63A GB2388863A GB991838A GB 991838 A GB991838 A GB 991838A GB 23888/63 A GB23888/63 A GB 23888/63A GB 2388863 A GB2388863 A GB 2388863A GB 991838 A GB991838 A GB 991838A
- Authority
- GB
- United Kingdom
- Prior art keywords
- piperazinyl
- prepared
- bis
- quinolyl
- chloro
- 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
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 title abstract 2
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 18
- HXEWMTXDBOQQKO-UHFFFAOYSA-N 4,7-dichloroquinoline Chemical compound ClC1=CC=NC2=CC(Cl)=CC=C21 HXEWMTXDBOQQKO-UHFFFAOYSA-N 0.000 abstract 10
- 238000000034 method Methods 0.000 abstract 7
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 abstract 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 4
- 150000003248 quinolines Chemical class 0.000 abstract 4
- 239000002253 acid Substances 0.000 abstract 3
- 239000000543 intermediate Substances 0.000 abstract 3
- 239000012280 lithium aluminium hydride Substances 0.000 abstract 3
- IQXXEPZFOOTTBA-UHFFFAOYSA-N 1-benzylpiperazine Chemical compound C=1C=CC=CC=1CN1CCNCC1 IQXXEPZFOOTTBA-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 229940111121 antirheumatic drug quinolines Drugs 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 abstract 2
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 150000002430 hydrocarbons Chemical group 0.000 abstract 2
- 239000012442 inert solvent Substances 0.000 abstract 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 abstract 2
- 231100000252 nontoxic Toxicity 0.000 abstract 2
- 230000003000 nontoxic effect Effects 0.000 abstract 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- NSMWYRLQHIXVAP-OLQVQODUSA-N (2r,5s)-2,5-dimethylpiperazine Chemical compound C[C@H]1CN[C@H](C)CN1 NSMWYRLQHIXVAP-OLQVQODUSA-N 0.000 abstract 1
- -1 1 - ethoxycarbonyl Chemical group 0.000 abstract 1
- RMIYQXDIOAJURM-UHFFFAOYSA-N 1,4-bis(4-benzylpiperazin-1-yl)butane-1,4-dione Chemical compound C1CN(CC=2C=CC=CC=2)CCN1C(=O)CCC(=O)N(CC1)CCN1CC1=CC=CC=C1 RMIYQXDIOAJURM-UHFFFAOYSA-N 0.000 abstract 1
- ZZHIDJWUJRKHGX-UHFFFAOYSA-N 1,4-bis(chloromethyl)benzene Chemical compound ClCC1=CC=C(CCl)C=C1 ZZHIDJWUJRKHGX-UHFFFAOYSA-N 0.000 abstract 1
- RCHDLEVSZBOHOS-UHFFFAOYSA-N 1,4-dichlorobut-2-yne Chemical compound ClCC#CCCl RCHDLEVSZBOHOS-UHFFFAOYSA-N 0.000 abstract 1
- FXMAMBJQSQEUBS-UHFFFAOYSA-N 1,5-bis(4-benzylpiperazin-1-yl)-3,3-dimethylpentane-1,5-dione Chemical compound C(C1=CC=CC=C1)N1CCN(CC1)C(CC(CC(=O)N1CCN(CC1)CC1=CC=CC=C1)(C)C)=O FXMAMBJQSQEUBS-UHFFFAOYSA-N 0.000 abstract 1
- ADAKNPVXJKBRJF-UHFFFAOYSA-N 1,5-bis(4-benzylpiperazin-1-yl)pentane-1,5-dione Chemical compound C1CN(CC=2C=CC=CC=2)CCN1C(=O)CCCC(=O)N(CC1)CCN1CC1=CC=CC=C1 ADAKNPVXJKBRJF-UHFFFAOYSA-N 0.000 abstract 1
- MYFHWWHAFYVFRA-UHFFFAOYSA-N 1,9-bis(4-benzylpiperazin-1-yl)nonane-1,9-dione Chemical compound C(C1=CC=CC=C1)N1CCN(CC1)C(CCCCCCCC(=O)N1CCN(CC1)CC1=CC=CC=C1)=O MYFHWWHAFYVFRA-UHFFFAOYSA-N 0.000 abstract 1
- HZOGSKJEJYLPFO-UHFFFAOYSA-N 1-(5-piperazin-1-ylpentyl)piperazine Chemical compound C1CNCCN1CCCCCN1CCNCC1 HZOGSKJEJYLPFO-UHFFFAOYSA-N 0.000 abstract 1
- MHHHCBZSHARREN-UHFFFAOYSA-N 1-(6-phenylhexan-2-yl)piperazine Chemical compound C(C1=CC=CC=C1)CCCC(C)N1CCNCC1 MHHHCBZSHARREN-UHFFFAOYSA-N 0.000 abstract 1
- IFYLTMDFBUEHSA-UHFFFAOYSA-N 1-benzyl-4-[4-(4-benzylpiperazin-1-yl)butyl]piperazine Chemical compound C(C1=CC=CC=C1)N1CCN(CC1)CCCCN1CCN(CC1)CC1=CC=CC=C1 IFYLTMDFBUEHSA-UHFFFAOYSA-N 0.000 abstract 1
- DUMGXPWKZLPOPS-UHFFFAOYSA-N 1-benzyl-4-[5-(4-benzylpiperazin-1-yl)-3,3-dimethylpentyl]piperazine Chemical compound C(C1=CC=CC=C1)N1CCN(CC1)CCC(CCN1CCN(CC1)CC1=CC=CC=C1)(C)C DUMGXPWKZLPOPS-UHFFFAOYSA-N 0.000 abstract 1
- LWEOFVINMVZGAS-UHFFFAOYSA-N 3-piperazin-1-ylpropan-1-ol Chemical compound OCCCN1CCNCC1 LWEOFVINMVZGAS-UHFFFAOYSA-N 0.000 abstract 1
- JZGUMSTXLPEMFW-UHFFFAOYSA-N 4,6-dichloroquinoline Chemical compound N1=CC=C(Cl)C2=CC(Cl)=CC=C21 JZGUMSTXLPEMFW-UHFFFAOYSA-N 0.000 abstract 1
- UKTYNFPTZDSBLR-UHFFFAOYSA-N 4-chloro-7-methoxyquinoline Chemical compound ClC1=CC=NC2=CC(OC)=CC=C21 UKTYNFPTZDSBLR-UHFFFAOYSA-N 0.000 abstract 1
- CDIIZULDSLKBKV-UHFFFAOYSA-N 4-chlorobutanoyl chloride Chemical compound ClCCCC(Cl)=O CDIIZULDSLKBKV-UHFFFAOYSA-N 0.000 abstract 1
- VZRDBLFATANAIO-UHFFFAOYSA-N 6-chloro-4-piperazin-1-ylquinoline Chemical compound C12=CC(Cl)=CC=C2N=CC=C1N1CCNCC1 VZRDBLFATANAIO-UHFFFAOYSA-N 0.000 abstract 1
- XUTWPKJOWFCPRF-MNOVXSKESA-N 7-chloro-4-[(2S,5R)-2,5-dimethylpiperazin-1-yl]quinoline Chemical compound ClC1=CC=C2C(=CC=NC2=C1)N1[C@H](CN[C@@H](C1)C)C XUTWPKJOWFCPRF-MNOVXSKESA-N 0.000 abstract 1
- UROPJUHDMCQLHY-UHFFFAOYSA-N 7-methoxy-4-piperazin-1-ylquinoline Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1N1CCNCC1 UROPJUHDMCQLHY-UHFFFAOYSA-N 0.000 abstract 1
- ORILYTVJVMAKLC-UHFFFAOYSA-N Adamantane Natural products C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000007868 Raney catalyst Substances 0.000 abstract 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 abstract 1
- 229910000564 Raney nickel Inorganic materials 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 229940124323 amoebicide Drugs 0.000 abstract 1
- 230000000507 anthelmentic effect Effects 0.000 abstract 1
- 229940124339 anthelmintic agent Drugs 0.000 abstract 1
- 239000000921 anthelmintic agent Substances 0.000 abstract 1
- 239000003430 antimalarial agent Substances 0.000 abstract 1
- 229940033495 antimalarials Drugs 0.000 abstract 1
- DLDJFQGPPSQZKI-UHFFFAOYSA-N but-2-yne-1,4-diol Chemical compound OCC#CCO DLDJFQGPPSQZKI-UHFFFAOYSA-N 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 238000005660 chlorination reaction Methods 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 150000005690 diesters Chemical class 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 abstract 1
- 229960003750 ethyl chloride Drugs 0.000 abstract 1
- LNOQURRKNJKKBU-UHFFFAOYSA-N ethyl piperazine-1-carboxylate Chemical compound CCOC(=O)N1CCNCC1 LNOQURRKNJKKBU-UHFFFAOYSA-N 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- HGEVGSTXQGZPCL-UHFFFAOYSA-N nonanedioyl dichloride Chemical compound ClC(=O)CCCCCCCC(Cl)=O HGEVGSTXQGZPCL-UHFFFAOYSA-N 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- YVOFTMXWTWHRBH-UHFFFAOYSA-N pentanedioyl dichloride Chemical compound ClC(=O)CCCC(Cl)=O YVOFTMXWTWHRBH-UHFFFAOYSA-N 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 abstract 1
- 229940075930 picrate Drugs 0.000 abstract 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 abstract 1
- 150000004885 piperazines Chemical class 0.000 abstract 1
- 125000004193 piperazinyl group Chemical group 0.000 abstract 1
- 229910052697 platinum Inorganic materials 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 229930195734 saturated hydrocarbon Natural products 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/38—Nitrogen atoms
- C07D215/42—Nitrogen atoms attached in position 4
- C07D215/46—Nitrogen atoms attached in position 4 with hydrocarbon radicals, substituted by nitrogen atoms, attached to said nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR900747A FR1392458A (fr) | 1962-06-14 | 1962-06-14 | Nouveaux dérivés de la quinoléine et leur préparation |
| FR908215A FR84902E (fr) | 1962-08-30 | 1962-08-30 | Nouveaux dérivés de la quinoléine et leur préparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB991838A true GB991838A (en) | 1965-05-12 |
Family
ID=26196161
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB23888/63A Expired GB991838A (en) | 1962-06-14 | 1963-06-14 | Quinoline derivatives |
Country Status (6)
| Country | Link |
|---|---|
| CH (1) | CH416628A (en:Method) |
| DK (4) | DK105341C (en:Method) |
| ES (1) | ES289028A1 (en:Method) |
| GB (1) | GB991838A (en:Method) |
| LU (1) | LU43730A1 (en:Method) |
| OA (1) | OA01392A (en:Method) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002094789A1 (en) * | 2001-05-21 | 2002-11-28 | F. Hoffmann-La Roche Ag | Quinoline derivatives as ligands for the neuropeptide y receptor |
| JP2019167331A (ja) * | 2018-03-22 | 2019-10-03 | 株式会社東芝 | アミン化合物、作業媒体及び水処理システム |
-
1963
- 1963-05-13 LU LU43730D patent/LU43730A1/xx unknown
- 1963-05-31 CH CH683563A patent/CH416628A/fr unknown
- 1963-06-14 DK DK417864AA patent/DK105341C/da active
- 1963-06-14 DK DK418064AA patent/DK105410C/da active
- 1963-06-14 GB GB23888/63A patent/GB991838A/en not_active Expired
- 1963-06-14 DK DK417964AA patent/DK105409C/da active
- 1963-06-14 DK DK281863AA patent/DK105340C/da active
- 1963-06-14 ES ES289028A patent/ES289028A1/es not_active Expired
-
1964
- 1964-12-31 OA OA51853A patent/OA01392A/xx unknown
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002094789A1 (en) * | 2001-05-21 | 2002-11-28 | F. Hoffmann-La Roche Ag | Quinoline derivatives as ligands for the neuropeptide y receptor |
| US6818767B2 (en) | 2001-05-21 | 2004-11-16 | Hoffmann-La Roche Inc. | Quinoline derivatives |
| CN100376557C (zh) * | 2001-05-21 | 2008-03-26 | 霍夫曼-拉罗奇有限公司 | 作为神经肽y受体的配体的喹啉衍生物 |
| JP2019167331A (ja) * | 2018-03-22 | 2019-10-03 | 株式会社東芝 | アミン化合物、作業媒体及び水処理システム |
Also Published As
| Publication number | Publication date |
|---|---|
| LU43730A1 (en:Method) | 1963-07-13 |
| CH416628A (fr) | 1966-07-15 |
| DK105410C (da) | 1966-09-26 |
| OA01392A (fr) | 1969-07-04 |
| ES289028A1 (es) | 1963-11-16 |
| DK105340C (da) | 1966-09-19 |
| DK105341C (da) | 1966-09-19 |
| DK105409C (da) | 1966-09-26 |
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