FI60012C - Foerfarande foer framstaellning av terapeutiskt aktiva 2-(7-klor-1,8-naftyridin-2-yl)-3-(karbamoyloxi)isoindolin-1-oner - Google Patents
Foerfarande foer framstaellning av terapeutiskt aktiva 2-(7-klor-1,8-naftyridin-2-yl)-3-(karbamoyloxi)isoindolin-1-oner Download PDFInfo
- Publication number
- FI60012C FI60012C FI760937A FI760937A FI60012C FI 60012 C FI60012 C FI 60012C FI 760937 A FI760937 A FI 760937A FI 760937 A FI760937 A FI 760937A FI 60012 C FI60012 C FI 60012C
- Authority
- FI
- Finland
- Prior art keywords
- chloro
- group
- carbon atoms
- naphthyridin
- isoindolin
- Prior art date
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- -1 7-CHLORO-1,8-NAPHTHYRIDIN-2-YL Chemical class 0.000 title claims description 43
- 230000001225 therapeutic effect Effects 0.000 title description 2
- 230000004913 activation Effects 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 claims description 44
- 150000001875 compounds Chemical class 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
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- 150000001412 amines Chemical class 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 239000012948 isocyanate Substances 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
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- CIEQWCUQFAGYED-UHFFFAOYSA-N [2-(7-chloro-1,8-naphthyridin-2-yl)-3-oxo-1h-isoindol-1-yl] piperidine-1-carboxylate Chemical compound N=1C2=NC(Cl)=CC=C2C=CC=1N(C(C1=CC=CC=C11)=O)C1OC(=O)N1CCCCC1 CIEQWCUQFAGYED-UHFFFAOYSA-N 0.000 description 1
- IOPREHRUSKGPPU-UHFFFAOYSA-N [6-chloro-2-(7-chloro-1,8-naphthyridin-2-yl)-3-oxo-1h-isoindol-1-yl] n-butylcarbamate Chemical compound C1=CC(Cl)=NC2=NC(N3C(C4=CC(Cl)=CC=C4C3=O)OC(=O)NCCCC)=CC=C21 IOPREHRUSKGPPU-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 208000012761 aggressive behavior Diseases 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 229940125681 anticonvulsant agent Drugs 0.000 description 1
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- 229940125715 antihistaminic agent Drugs 0.000 description 1
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- XTKDAFGWCDAMPY-UHFFFAOYSA-N azaperone Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CCN(C=2N=CC=CC=2)CC1 XTKDAFGWCDAMPY-UHFFFAOYSA-N 0.000 description 1
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- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
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- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 1
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- 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
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- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- WDCDAAMJNUHOIY-UHFFFAOYSA-N ethyl acetate;2-propan-2-yloxypropane Chemical compound CCOC(C)=O.CC(C)OC(C)C WDCDAAMJNUHOIY-UHFFFAOYSA-N 0.000 description 1
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- BLNWTAHYTCHDJH-UHFFFAOYSA-O hydroxy(oxo)azanium Chemical compound O[NH+]=O BLNWTAHYTCHDJH-UHFFFAOYSA-O 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical group C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 description 1
- 238000009533 lab test Methods 0.000 description 1
- 230000006742 locomotor activity Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- FMNXOVQDRMSXLX-UHFFFAOYSA-N methyl 2-[[2-(7-chloro-1,8-naphthyridin-2-yl)-3-oxo-1h-isoindol-1-yl]oxycarbonylamino]acetate Chemical compound C1=CC(Cl)=NC2=NC(N3C(C4=CC=CC=C4C3=O)OC(=O)NCC(=O)OC)=CC=C21 FMNXOVQDRMSXLX-UHFFFAOYSA-N 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- OCDPLMCWDJXNTG-UHFFFAOYSA-N n-methyl-n-pentylcarbamoyl chloride Chemical compound CCCCCN(C)C(Cl)=O OCDPLMCWDJXNTG-UHFFFAOYSA-N 0.000 description 1
- 239000003176 neuroleptic agent Substances 0.000 description 1
- 230000000701 neuroleptic effect Effects 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 1
- 229940100684 pentylamine Drugs 0.000 description 1
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 238000011197 physicochemical method Methods 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 230000000506 psychotropic effect Effects 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 229960005453 strychnine Drugs 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
- A61K9/2059—Starch, including chemically or physically modified derivatives; Amylose; Amylopectin; Dextrin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/08—Preparation of carboxylic acids or their salts, halides or anhydrides from nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/54—Preparation of carboxylic acid anhydrides
- C07C51/56—Preparation of carboxylic acid anhydrides from organic acids, their salts, their esters or their halides, e.g. by carboxylation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Neurology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Anesthesiology (AREA)
- Pain & Pain Management (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI811276A FI63589C (fi) | 1976-02-11 | 1981-04-23 | Foerfarande foer framstaellning av terapeutiskt aktiva 6-(7-klor-1,8-naftyridin-2-yl)-5-karbamoyloxi-7-oxo-6,7-dihydro-5h-pyrrolo(3,4-b)pyraziner |
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7510756 | 1975-04-07 | ||
| FR7510756A FR2321290A1 (fr) | 1975-04-07 | 1975-04-07 | Nouveaux derives de l'isoindoline, leur preparation et les compositions qui les contiennent |
| FR7603774 | 1976-02-11 | ||
| FR7603773A FR2340733A2 (fr) | 1976-02-11 | 1976-02-11 | Nouveaux derives de l'isoindoline, leur preparation et les compositions qui les contiennent |
| FR7603773 | 1976-02-11 | ||
| FR7603774A FR2340731A1 (fr) | 1976-02-11 | 1976-02-11 | Nouveaux composes heterocycliques, leur preparation et les compositions qui les contiennent |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI760937A7 FI760937A7 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-10-08 |
| FI60012B FI60012B (fi) | 1981-07-31 |
| FI60012C true FI60012C (fi) | 1981-11-10 |
Family
ID=27250439
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI760937A FI60012C (fi) | 1975-04-07 | 1976-04-07 | Foerfarande foer framstaellning av terapeutiskt aktiva 2-(7-klor-1,8-naftyridin-2-yl)-3-(karbamoyloxi)isoindolin-1-oner |
Country Status (29)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1265803A (fr) * | 1985-07-11 | 1990-02-13 | Claude Cotrel | Amides substitues, leur preparation et les medicaments qui les contiennent |
| DE10042093A1 (de) * | 2000-08-26 | 2002-03-07 | Dresden Arzneimittel | Antikonvulsiv wirkende 6,7-Dihydro-pyrrolo[3,4-d]pyridin-5-one und Verfahren zu deren Darstellung |
| US7521451B2 (en) * | 2002-11-26 | 2009-04-21 | Maruishi Pharmaceutical Co., Ltd. | Isoindoline derivative |
| WO2007080430A1 (en) * | 2006-01-16 | 2007-07-19 | Generics [Uk] Limited | Novel process |
| WO2014114779A1 (en) | 2013-01-28 | 2014-07-31 | H. Lundbeck A/S | N-substituted-5-substituted phthalamic acids as sortilin inhibitors |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| OA04700A (fr) * | 1973-05-15 | 1980-07-31 | Rhone Poulenc Sa | Nouveaux dérivés de la naphtyridine et leur procédé de préparation. |
-
1976
- 1976-03-26 OA OA55782A patent/OA05287A/xx unknown
- 1976-03-30 NL NL7603307A patent/NL7603307A/xx not_active Application Discontinuation
- 1976-03-31 CS CS7700002623A patent/CS186747B2/cs unknown
- 1976-03-31 CS CS7700002624A patent/CS186748B2/cs unknown
- 1976-03-31 CS CS7600002084A patent/CS186734B2/cs unknown
- 1976-04-05 DD DD192209A patent/DD123605A5/xx unknown
- 1976-04-05 GB GB13703/76A patent/GB1483996A/en not_active Expired
- 1976-04-05 JP JP51038103A patent/JPS51122094A/ja active Granted
- 1976-04-05 CA CA249,577A patent/CA1072957A/fr not_active Expired
- 1976-04-05 US US05/673,868 patent/US4086348A/en not_active Expired - Lifetime
- 1976-04-05 IE IE704/76A patent/IE42973B1/en unknown
- 1976-04-05 IL IL49344A patent/IL49344A/xx unknown
- 1976-04-05 PH PH18289A patent/PH14015A/en unknown
- 1976-04-05 CY CY1085A patent/CY1085A/xx unknown
- 1976-04-06 DK DK162976A patent/DK162976A/da not_active IP Right Cessation
- 1976-04-06 MX MX14476U patent/MX3138E/es unknown
- 1976-04-06 SU SU762339152A patent/SU648102A3/ru active
- 1976-04-06 NO NO761168A patent/NO144019C/no unknown
- 1976-04-06 PT PT64976A patent/PT64976B/pt unknown
- 1976-04-06 SE SE7604044A patent/SE421793B/xx not_active IP Right Cessation
- 1976-04-06 YU YU00869/76A patent/YU86976A/xx unknown
- 1976-04-06 SE SE7604044D patent/SE7604044L/xx not_active Application Discontinuation
- 1976-04-06 LU LU74703A patent/LU74703A1/xx unknown
- 1976-04-06 CH CH1212178A patent/CH614209A5/fr not_active IP Right Cessation
- 1976-04-06 CH CH430576A patent/CH613453A5/xx not_active IP Right Cessation
- 1976-04-07 HU HU76RO886A patent/HU176315B/hu unknown
- 1976-04-07 PL PL1976202792A patent/PL100988B1/pl unknown
- 1976-04-07 ES ES446762A patent/ES446762A1/es not_active Expired
- 1976-04-07 AT AT249776A patent/AT348524B/de not_active IP Right Cessation
- 1976-04-07 PL PL1976188560A patent/PL100184B1/pl unknown
- 1976-04-07 PL PL1976202791A patent/PL100987B1/pl unknown
- 1976-04-07 DE DE19762615067 patent/DE2615067A1/de not_active Ceased
- 1976-04-07 FI FI760937A patent/FI60012C/fi not_active IP Right Cessation
- 1976-04-07 AR AR262814A patent/AR214286A1/es active
- 1976-06-14 ES ES448847A patent/ES448847A1/es not_active Expired
- 1976-09-28 AR AR264893A patent/AR213739A1/es active
- 1976-09-30 AR AR264924A patent/AR214055A1/es active
-
1977
- 1977-04-21 SU SU772473623A patent/SU638258A3/ru active
- 1977-04-21 SU SU772473622A patent/SU637082A3/ru active
-
1980
- 1980-09-25 HK HK545/80A patent/HK54580A/xx unknown
-
1982
- 1982-06-15 YU YU01304/82A patent/YU130482A/xx unknown
- 1982-06-15 YU YU01305/82A patent/YU130582A/xx unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: RHONE- POULENC INDUSTRIES |