GB986350A - Aminoquinoline derivatives - Google Patents
Aminoquinoline derivativesInfo
- Publication number
- GB986350A GB986350A GB48466/62A GB4846662A GB986350A GB 986350 A GB986350 A GB 986350A GB 48466/62 A GB48466/62 A GB 48466/62A GB 4846662 A GB4846662 A GB 4846662A GB 986350 A GB986350 A GB 986350A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compound
- propyl
- acetyl
- chloro
- amino
- 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
- 150000005010 aminoquinolines Chemical class 0.000 title abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 10
- 125000000217 alkyl group Chemical group 0.000 abstract 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 abstract 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 abstract 4
- 239000002253 acid Substances 0.000 abstract 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
- -1 N-acetyl compound Chemical class 0.000 abstract 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- HXEWMTXDBOQQKO-UHFFFAOYSA-N 4,7-dichloroquinoline Chemical compound ClC1=CC=NC2=CC(Cl)=CC=C21 HXEWMTXDBOQQKO-UHFFFAOYSA-N 0.000 abstract 2
- HFDLDPJYCIEXJP-UHFFFAOYSA-N 6-methoxyquinoline Chemical compound N1=CC=CC2=CC(OC)=CC=C21 HFDLDPJYCIEXJP-UHFFFAOYSA-N 0.000 abstract 2
- 125000005236 alkanoylamino group Chemical group 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 229940058934 aminoquinoline antimalarials Drugs 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 2
- 125000006239 protecting group Chemical group 0.000 abstract 2
- GJKZKBZGAVBCGF-QMMMGPOBSA-N (2S)-2-[(7-chloroquinolin-4-yl)amino]propan-1-ol Chemical class ClC1=CC=C2C(N[C@H](CO)C)=CC=NC2=C1 GJKZKBZGAVBCGF-QMMMGPOBSA-N 0.000 abstract 1
- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 abstract 1
- KGVASZPVUAGZRP-UHFFFAOYSA-N 2-(quinolin-4-ylamino)propan-1-ol Chemical class C1=CC=C2C(NC(CO)C)=CC=NC2=C1 KGVASZPVUAGZRP-UHFFFAOYSA-N 0.000 abstract 1
- BKMMTJMQCTUHRP-UHFFFAOYSA-N 2-aminopropan-1-ol Chemical compound CC(N)CO BKMMTJMQCTUHRP-UHFFFAOYSA-N 0.000 abstract 1
- BUVGUZAVGALTEW-UHFFFAOYSA-N 3-[4-(2-cyanoethyl)-1,4-diazepan-1-yl]propanenitrile Chemical compound C(#N)CCN1CCN(CCC1)CCC#N BUVGUZAVGALTEW-UHFFFAOYSA-N 0.000 abstract 1
- SDXJLGYLBHKWLB-UHFFFAOYSA-N 3-amino-7-[4-(5-amino-6-oxo-4-quinolin-4-ylheptyl)piperazin-1-yl]-4-quinolin-4-ylheptan-2-one Chemical compound N1=CC=C(C2=CC=CC=C12)C(CCCN1CCN(CC1)CCCC(C(N)C(C)=O)C1=CC=NC2=CC=CC=C12)C(N)C(C)=O SDXJLGYLBHKWLB-UHFFFAOYSA-N 0.000 abstract 1
- APIVVDFBBPFBDZ-UHFFFAOYSA-N 3-amino-n,n-dimethylbenzenesulfonamide Chemical compound CN(C)S(=O)(=O)C1=CC=CC(N)=C1 APIVVDFBBPFBDZ-UHFFFAOYSA-N 0.000 abstract 1
- WQGZORDCTSOCSG-UHFFFAOYSA-N 4-(2-aminoquinolin-4-yl)pentan-1-ol Chemical compound OCCCC(C)C1=CC(=NC2=CC=CC=C12)N WQGZORDCTSOCSG-UHFFFAOYSA-N 0.000 abstract 1
- KNDOFJFSHZCKGT-UHFFFAOYSA-N 4-chloroquinoline Chemical compound C1=CC=C2C(Cl)=CC=NC2=C1 KNDOFJFSHZCKGT-UHFFFAOYSA-N 0.000 abstract 1
- 150000005653 4-chloroquinolines Chemical class 0.000 abstract 1
- CVUUCFIVYYDLHL-UHFFFAOYSA-N 7-chloroquinolin-2-amine Chemical class C1=CC(Cl)=CC2=NC(N)=CC=C21 CVUUCFIVYYDLHL-UHFFFAOYSA-N 0.000 abstract 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 abstract 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 abstract 1
- DMOZWSIBZNRALP-UHFFFAOYSA-N N,N-dimethyl-4-oxo-1H-quinoline-7-sulfonamide Chemical compound CN(S(=O)(=O)C1=CC=C2C(=CC=NC2=C1)O)C DMOZWSIBZNRALP-UHFFFAOYSA-N 0.000 abstract 1
- HVRGOKDYSGCXTO-UHFFFAOYSA-N N-[1-[4-(2-hydroxyiminopropyl)-1,4-diazepan-1-yl]propan-2-ylidene]hydroxylamine Chemical compound N(O)=C(CN1CCN(CCC1)CC(C)=NO)C HVRGOKDYSGCXTO-UHFFFAOYSA-N 0.000 abstract 1
- 125000003047 N-acetyl group Chemical group 0.000 abstract 1
- YMQMWNPOHKVAKZ-UHFFFAOYSA-N [6-(2-aminoquinolin-4-yl)-4-methyl-6-oxohexyl] methanesulfonate Chemical compound CS(=O)(=O)OCCCC(C)CC(=O)C1=CC(=NC2=CC=CC=C12)N YMQMWNPOHKVAKZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 230000003569 amebicidal effect Effects 0.000 abstract 1
- 230000000507 anthelmentic effect Effects 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 230000000078 anti-malarial effect Effects 0.000 abstract 1
- 230000003356 anti-rheumatic effect Effects 0.000 abstract 1
- 239000003430 antimalarial agent Substances 0.000 abstract 1
- 239000002775 capsule Substances 0.000 abstract 1
- 125000001589 carboacyl group Chemical group 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 238000000576 coating method Methods 0.000 abstract 1
- LTMHNWPUDSTBKD-UHFFFAOYSA-N diethyl 2-(ethoxymethylidene)propanedioate Chemical compound CCOC=C(C(=O)OCC)C(=O)OCC LTMHNWPUDSTBKD-UHFFFAOYSA-N 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- YBXQIAUGXPWAMZ-UHFFFAOYSA-N ethyl 7-(dimethylsulfamoyl)-4-oxo-1H-quinoline-3-carboxylate Chemical compound C(=O)(OCC)C=1C=NC2=CC(=CC=C2C1O)S(N(C)C)(=O)=O YBXQIAUGXPWAMZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000008187 granular material Substances 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- 239000008016 pharmaceutical coating Substances 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
- 239000006187 pill Substances 0.000 abstract 1
- 150000004885 piperazines Chemical class 0.000 abstract 1
- 239000000843 powder Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 238000007127 saponification reaction Methods 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 239000000829 suppository Substances 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
- 239000006188 syrup Substances 0.000 abstract 1
- 235000020357 syrup Nutrition 0.000 abstract 1
- 239000003826 tablet Substances 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
-
- 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
- C07D215/36—Sulfur atoms
-
- 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
-
- 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
- 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
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
- C07D215/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3 with oxygen atoms in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J17/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, having an oxygen-containing hetero ring not condensed with the cyclopenta(a)hydrophenanthrene skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/0055—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the 17-beta position being substituted by an uninterrupted chain of at least three carbon atoms which may or may not be branched, e.g. cholane or cholestane derivatives, optionally cyclised, e.g. 17-beta-phenyl or 17-beta-furyl derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J51/00—Normal steroids with unmodified cyclopenta(a)hydrophenanthrene skeleton not provided for in groups C07J1/00 - C07J43/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR883457 | 1961-12-29 | ||
FR891650 | 1962-03-20 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB986350A true GB986350A (en) | 1965-03-17 |
Family
ID=26193748
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB48466/62A Expired GB986350A (en) | 1961-12-29 | 1962-12-21 | Aminoquinoline derivatives |
Country Status (11)
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4515947A (en) * | 1982-08-11 | 1985-05-07 | Eastman Kodak Company | Cyanoalkylpiperazines and methods for their preparation and use |
US5182387A (en) * | 1991-10-30 | 1993-01-26 | Merrell Dow Pharmaceuticals Inc. | Bis-dibenzoazepine compounds |
EP2030967A1 (de) * | 2007-08-31 | 2009-03-04 | Sika Technology AG | Hydroxylgruppen aufweisende Aldimine und Aldimin enthaltende Zusammensetzungen |
IN2012DE00661A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 2012-03-07 | 2015-08-21 | Univ Delhi |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR1012751A (fr) * | 1949-01-24 | 1952-07-17 | Rhone Poulenc Sa | Nouveau dérivé de la pipérazine et de la quinoléïne et son procédé de préparation |
US2901484A (en) * | 1957-03-04 | 1959-08-25 | Abbott Lab | Bis-quinoliniums |
US3020283A (en) * | 1958-10-20 | 1962-02-06 | Abbott Lab | Bis-lepidines |
-
0
- NL NL106667D patent/NL106667C/xx active
- BE BE626239D patent/BE626239A/xx unknown
- FR FR82308D patent/FR82308A/fr not_active Expired
- FR FR82307D patent/FR82307A/fr not_active Expired
-
1960
- 1960-07-20 FR FR833410A patent/FR42M/fr not_active Expired
-
1961
- 1961-02-13 DE DEL38191A patent/DE1156803B/de active Pending
- 1961-12-21 DK DK110364AA patent/DK106147C/da active
-
1962
- 1962-04-19 LU LU41571D patent/LU41571A1/xx unknown
- 1962-06-08 US US200953A patent/US3196155A/en not_active Expired - Lifetime
- 1962-07-06 DE DER33082A patent/DE1196202B/de active Pending
- 1962-08-13 CH CH971062A patent/CH453360A/fr unknown
- 1962-08-31 AT AT469463A patent/AT242141B/de active
- 1962-09-15 ES ES280829A patent/ES280829A1/es not_active Expired
- 1962-12-21 DK DK558762AA patent/DK106146C/da active
- 1962-12-21 GB GB48466/62A patent/GB986350A/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
ES280829A1 (es) | 1963-01-16 |
FR42M (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1960-11-28 |
DE1196202B (de) | 1965-07-08 |
FR82308A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1900-01-01 |
DK106147C (da) | 1966-12-27 |
LU41571A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1962-06-19 |
AT242141B (de) | 1965-08-25 |
US3196155A (en) | 1965-07-20 |
BE626239A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1900-01-01 |
NL106667C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1900-01-01 |
DE1156803B (de) | 1963-11-07 |
CH453360A (fr) | 1968-06-14 |
DK106146C (da) | 1966-12-27 |
FR82307A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1900-01-01 |
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