DE2143744A1 - 3,4-dihydro-2h-isochinolin-1-one und verfahren zu ihrer herstellung - Google Patents
3,4-dihydro-2h-isochinolin-1-one und verfahren zu ihrer herstellungInfo
- Publication number
- DE2143744A1 DE2143744A1 DE2143744A DE2143744A DE2143744A1 DE 2143744 A1 DE2143744 A1 DE 2143744A1 DE 2143744 A DE2143744 A DE 2143744A DE 2143744 A DE2143744 A DE 2143744A DE 2143744 A1 DE2143744 A1 DE 2143744A1
- Authority
- DE
- Germany
- Prior art keywords
- dihydro
- phenyl
- isoquinolin
- carbon atoms
- radical
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 27
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- YWPMKTWUFVOFPL-UHFFFAOYSA-N 3,4-dihydro-2h-isoquinolin-1-one Chemical compound C1=CC=C2C(=O)NCCC2=C1 YWPMKTWUFVOFPL-UHFFFAOYSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- 238000011282 treatment Methods 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 125000002837 carbocyclic group Chemical group 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
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- 238000010992 reflux Methods 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
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- 241001465754 Metazoa Species 0.000 description 3
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- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 3
- 210000004351 coronary vessel Anatomy 0.000 description 3
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- 150000002148 esters Chemical class 0.000 description 3
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
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- 239000007858 starting material Substances 0.000 description 3
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- 150000003585 thioureas Chemical class 0.000 description 3
- 150000003672 ureas Chemical class 0.000 description 3
- IOYIDSMWPLNHRC-UHFFFAOYSA-N 2h-isoquinoline-1-thione Chemical class C1=CC=C2C(S)=NC=CC2=C1 IOYIDSMWPLNHRC-UHFFFAOYSA-N 0.000 description 2
- PGVRVOLZSPHFNU-UHFFFAOYSA-N 4-benzyl-3,4-dihydro-2h-isoquinolin-1-one Chemical compound C12=CC=CC=C2C(=O)NCC1CC1=CC=CC=C1 PGVRVOLZSPHFNU-UHFFFAOYSA-N 0.000 description 2
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- VDBNYAPERZTOOF-UHFFFAOYSA-N isoquinolin-1(2H)-one Chemical compound C1=CC=C2C(=O)NC=CC2=C1 VDBNYAPERZTOOF-UHFFFAOYSA-N 0.000 description 2
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- ANTSCNMPPGJYLG-UHFFFAOYSA-N chlordiazepoxide Chemical compound O=N=1CC(NC)=NC2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 ANTSCNMPPGJYLG-UHFFFAOYSA-N 0.000 description 1
- 229960004782 chlordiazepoxide Drugs 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
- KNHUKKLJHYUCFP-UHFFFAOYSA-N clofibrate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 KNHUKKLJHYUCFP-UHFFFAOYSA-N 0.000 description 1
- 229960001214 clofibrate Drugs 0.000 description 1
- 239000003026 cod liver oil Substances 0.000 description 1
- 235000012716 cod liver oil Nutrition 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 208000029078 coronary artery disease Diseases 0.000 description 1
- 239000003218 coronary vasodilator agent Substances 0.000 description 1
- 229960003529 diazepam Drugs 0.000 description 1
- AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- YAGKRVSRTSUGEY-UHFFFAOYSA-N ferricyanide Chemical compound [Fe+3].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] YAGKRVSRTSUGEY-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 229960004580 glibenclamide Drugs 0.000 description 1
- ZNNLBTZKUZBEKO-UHFFFAOYSA-N glyburide Chemical compound COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)NC2CCCCC2)C=C1 ZNNLBTZKUZBEKO-UHFFFAOYSA-N 0.000 description 1
- QFWPJPIVLCBXFJ-UHFFFAOYSA-N glymidine Chemical compound N1=CC(OCCOC)=CN=C1NS(=O)(=O)C1=CC=CC=C1 QFWPJPIVLCBXFJ-UHFFFAOYSA-N 0.000 description 1
- 229960004440 glymidine Drugs 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000007902 hard capsule Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000000055 hyoplipidemic effect Effects 0.000 description 1
- 208000006575 hypertriglyceridemia Diseases 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- 230000004807 localization Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229960004815 meprobamate Drugs 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- CMUOJBJRZUHRMU-UHFFFAOYSA-N nitrourea Chemical compound NC(=O)N[N+]([O-])=O CMUOJBJRZUHRMU-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 229960001989 prenylamine Drugs 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 1
- 229960003147 reserpine Drugs 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
- 229960005371 tolbutamide Drugs 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/20—Spiro-condensed ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C265/00—Derivatives of isocyanic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/004—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with organometalhalides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/213—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing six-membered aromatic rings
- C07C49/215—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing six-membered aromatic rings polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems 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 carbon atoms of the nitrogen-containing ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems 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 carbon atoms of the nitrogen-containing ring
- C07D217/24—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)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Priority Applications (14)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2143744A DE2143744A1 (de) | 1971-09-01 | 1971-09-01 | 3,4-dihydro-2h-isochinolin-1-one und verfahren zu ihrer herstellung |
CA148,981A CA983039A (en) | 1971-09-01 | 1972-08-09 | 3,4-dihydro-2h-isoquinoline-1-ones and process for preparing them |
DD165086A DD102147A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-09-01 | 1972-08-16 | |
NL7211626A NL7211626A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-09-01 | 1972-08-25 | |
BG023337A BG19799A3 (bg) | 1971-09-01 | 1972-08-28 | Метод за получаване на 3,4-дихидро-2н-изохинолин-1-они |
BG023338A BG19375A3 (bg) | 1971-09-01 | 1972-08-28 | Метод за получаване на 3,4-1н-изохиномин-1-они |
BG021265A BG20410A3 (bg) | 1971-09-01 | 1972-08-28 | Метод за получаване на 3,4-дихидро-2н- изохинолин-1-они |
IL40249A IL40249A0 (en) | 1971-09-01 | 1972-08-29 | 3,4-dihydro-2h-isoquinoline-1-ones and process for preparing them |
AU46103/72A AU4610372A (en) | 1971-09-01 | 1972-08-30 | 3, 4-dihydro-2h-isoquinoline-1-ones and process for preparing them |
ZA725996A ZA725996B (en) | 1971-09-01 | 1972-08-31 | 3,4-dihydro-2h-isoquinoline-1-ones and process for preparing them |
FR7230950A FR2151043A1 (en) | 1971-09-01 | 1972-08-31 | 3,4-dihydro-2h-isoquinoline-1-ones - useful for lowering of cholesterol - and triglyceride level in serum |
JP47087840A JPS4834886A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-09-01 | 1972-09-01 | |
HUHO1512A HU165204B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-09-01 | 1972-09-01 | |
BE788322D BE788322A (fr) | 1971-09-01 | 1972-09-01 | 3,4-dihydro-2h-isoquinoleine-1-ones et medicaments qui en contiennent |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2143744A DE2143744A1 (de) | 1971-09-01 | 1971-09-01 | 3,4-dihydro-2h-isochinolin-1-one und verfahren zu ihrer herstellung |
Publications (1)
Publication Number | Publication Date |
---|---|
DE2143744A1 true DE2143744A1 (de) | 1973-03-08 |
Family
ID=5818353
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE2143744A Pending DE2143744A1 (de) | 1971-09-01 | 1971-09-01 | 3,4-dihydro-2h-isochinolin-1-one und verfahren zu ihrer herstellung |
Country Status (12)
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2281763A1 (fr) * | 1974-08-14 | 1976-03-12 | Hoechst Ag | 3,4-dihydro-2h-isoquinoleine-1-ones a substituant basique, leur procede de preparation et leurs applications |
EP0167820A3 (en) * | 1984-06-14 | 1986-09-17 | Bayer Ag | Process for the preparation of optionally substituted benz(c,d)-indol-2-ones (naphtholactames) |
WO2008070496A3 (en) * | 2006-12-01 | 2008-09-18 | Bristol Myers Squibb Co | N- ( (3-benzyl) -2, 2- (bis-phenyl) -propan-1-amine derivatives as cetp inhibitors for the treatment of atherosclerosis and cardiovascular diseases |
CN104822687A (zh) * | 2012-10-02 | 2015-08-05 | 英特穆恩公司 | 抗纤维化吡啶酮类 |
USRE47142E1 (en) | 2008-06-03 | 2018-11-27 | Intermune, Inc. | Compounds and methods for treating inflammatory and fibrotic disorders |
US10233195B2 (en) | 2014-04-02 | 2019-03-19 | Intermune, Inc. | Anti-fibrotic pyridinones |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5650682B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1974-03-25 | 1981-12-01 | ||
GB1576511A (en) * | 1977-03-29 | 1980-10-08 | Parcor | Thieno(2,3 - c) and (3,2 - c) pyridines process for their preparation and therapeutic applications thereof |
-
1971
- 1971-09-01 DE DE2143744A patent/DE2143744A1/de active Pending
-
1972
- 1972-08-09 CA CA148,981A patent/CA983039A/en not_active Expired
- 1972-08-16 DD DD165086A patent/DD102147A5/xx unknown
- 1972-08-25 NL NL7211626A patent/NL7211626A/xx unknown
- 1972-08-28 BG BG023338A patent/BG19375A3/xx unknown
- 1972-08-28 BG BG023337A patent/BG19799A3/xx unknown
- 1972-08-28 BG BG021265A patent/BG20410A3/xx unknown
- 1972-08-29 IL IL40249A patent/IL40249A0/xx unknown
- 1972-08-30 AU AU46103/72A patent/AU4610372A/en not_active Expired
- 1972-08-31 ZA ZA725996A patent/ZA725996B/xx unknown
- 1972-08-31 FR FR7230950A patent/FR2151043A1/fr not_active Withdrawn
- 1972-09-01 HU HUHO1512A patent/HU165204B/hu unknown
- 1972-09-01 BE BE788322D patent/BE788322A/xx unknown
- 1972-09-01 JP JP47087840A patent/JPS4834886A/ja active Pending
Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2281763A1 (fr) * | 1974-08-14 | 1976-03-12 | Hoechst Ag | 3,4-dihydro-2h-isoquinoleine-1-ones a substituant basique, leur procede de preparation et leurs applications |
EP0167820A3 (en) * | 1984-06-14 | 1986-09-17 | Bayer Ag | Process for the preparation of optionally substituted benz(c,d)-indol-2-ones (naphtholactames) |
WO2008070496A3 (en) * | 2006-12-01 | 2008-09-18 | Bristol Myers Squibb Co | N- ( (3-benzyl) -2, 2- (bis-phenyl) -propan-1-amine derivatives as cetp inhibitors for the treatment of atherosclerosis and cardiovascular diseases |
US8404896B2 (en) | 2006-12-01 | 2013-03-26 | Bristol-Myers Squibb Company | N-((3-benzyl)-2,2-(bis-phenyl)-propan-1-amine derivatives as CETP inhibitors for the treatment of atherosclerosis and cardiovascular diseases |
US9102599B2 (en) | 2006-12-01 | 2015-08-11 | Bristol-Myers Squibb Company | N-((3-benzyl)-2,2-(bis-phenyl)-propan-1-amine derivatives as CETP inhibitors for the treatment of atherosclerosis and cardiovascular diseases |
USRE47142E1 (en) | 2008-06-03 | 2018-11-27 | Intermune, Inc. | Compounds and methods for treating inflammatory and fibrotic disorders |
EP2903991A4 (en) * | 2012-10-02 | 2016-09-07 | Intermune Inc | ANTIFIBROTIC PYRIDINONE |
US9675593B2 (en) | 2012-10-02 | 2017-06-13 | Intermune, Inc. | Anti-fibrotic pyridinones |
CN104822687A (zh) * | 2012-10-02 | 2015-08-05 | 英特穆恩公司 | 抗纤维化吡啶酮类 |
US10376497B2 (en) | 2012-10-02 | 2019-08-13 | Intermune, Inc. | Anti-fibrotic pyridinones |
US10898474B2 (en) | 2012-10-02 | 2021-01-26 | Intermune, Inc. | Anti-fibrotic pyridinones |
US10233195B2 (en) | 2014-04-02 | 2019-03-19 | Intermune, Inc. | Anti-fibrotic pyridinones |
US10544161B2 (en) | 2014-04-02 | 2020-01-28 | Intermune, Inc. | Anti-fibrotic pyridinones |
Also Published As
Publication number | Publication date |
---|---|
ZA725996B (en) | 1973-06-27 |
NL7211626A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1973-03-05 |
FR2151043A1 (en) | 1973-04-13 |
BG20410A3 (bg) | 1975-11-05 |
BG19799A3 (bg) | 1975-10-10 |
JPS4834886A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1973-05-22 |
IL40249A0 (en) | 1972-10-29 |
AU4610372A (en) | 1974-03-07 |
CA983039A (en) | 1976-02-03 |
BE788322A (fr) | 1973-03-01 |
HU165204B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-07-27 |
DD102147A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1973-12-05 |
BG19375A3 (bg) | 1975-06-15 |
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