FI65621C - Foerfarande foer framstaellning av som cns-aktiva medel anvaendbara 2-(4,4-difluorfenyl-butyl)-6h-oktahydropyrazino-(1,2-c) pyrimidin-6-oner - Google Patents
Foerfarande foer framstaellning av som cns-aktiva medel anvaendbara 2-(4,4-difluorfenyl-butyl)-6h-oktahydropyrazino-(1,2-c) pyrimidin-6-oner Download PDFInfo
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- FI65621C FI65621C FI782370A FI782370A FI65621C FI 65621 C FI65621 C FI 65621C FI 782370 A FI782370 A FI 782370A FI 782370 A FI782370 A FI 782370A FI 65621 C FI65621 C FI 65621C
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- -1 4,4-DIFLUORPHENYL-BUTYL Chemical class 0.000 title claims description 13
- 241000948268 Meda Species 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 87
- 238000000034 method Methods 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 21
- 238000002360 preparation method Methods 0.000 claims description 17
- 150000002431 hydrogen Chemical class 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 239000001273 butane Substances 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000000203 mixture Substances 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 238000002474 experimental method Methods 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 238000009835 boiling Methods 0.000 description 8
- CAWHJQAVHZEVTJ-UHFFFAOYSA-N methylpyrazine Chemical class CC1=CN=CC=N1 CAWHJQAVHZEVTJ-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- KANZWHBYRHQMKZ-UHFFFAOYSA-N 2-ethenylpyrazine Chemical compound C=CC1=CN=CC=N1 KANZWHBYRHQMKZ-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
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- 230000006399 behavior Effects 0.000 description 5
- DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical class O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 description 4
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 3
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- XHFGWHUWQXTGAT-UHFFFAOYSA-N dimethylamine hydrochloride Natural products CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 3
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- YTEODLDKOVRIPV-UHFFFAOYSA-N n,n-dimethyl-2-(5-methylpyrazin-2-yl)ethanamine Chemical compound CN(C)CCC1=CN=C(C)C=N1 YTEODLDKOVRIPV-UHFFFAOYSA-N 0.000 description 3
- BOCWITWPYWEWPR-UHFFFAOYSA-N n,n-dimethyl-2-pyrazin-2-ylethanamine Chemical compound CN(C)CCC1=CN=CC=N1 BOCWITWPYWEWPR-UHFFFAOYSA-N 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
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- 239000002904 solvent Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- LCZUOKDVTBMCMX-UHFFFAOYSA-N 2,5-Dimethylpyrazine Chemical compound CC1=CN=C(C)C=N1 LCZUOKDVTBMCMX-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
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- 229910021529 ammonia Inorganic materials 0.000 description 2
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- 210000003205 muscle Anatomy 0.000 description 1
- ACYBVNYNIZTUIL-UHFFFAOYSA-N n'-benzylethane-1,2-diamine Chemical compound NCCNCC1=CC=CC=C1 ACYBVNYNIZTUIL-UHFFFAOYSA-N 0.000 description 1
- NOHCNCYWYBZEDT-UHFFFAOYSA-N n,n-dimethyl-2-pyrazin-2-ylpropan-1-amine Chemical compound CN(C)CC(C)C1=CN=CC=N1 NOHCNCYWYBZEDT-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- GPGCODUJSUBUFQ-UHFFFAOYSA-N n-ethyl-2-pyrazin-2-ylethanamine Chemical compound CCNCCC1=CN=CC=N1 GPGCODUJSUBUFQ-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229940001470 psychoactive drug Drugs 0.000 description 1
- 239000004089 psychotropic agent Substances 0.000 description 1
- 239000000700 radioactive tracer Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/12—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Rheumatology (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Child & Adolescent Psychology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Anesthesiology (AREA)
- Nutrition Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3690477 | 1977-09-05 | ||
| GB3690477 | 1977-09-05 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI782370A7 FI782370A7 (fi) | 1979-03-06 |
| FI65621B FI65621B (fi) | 1984-02-29 |
| FI65621C true FI65621C (fi) | 1984-06-11 |
Family
ID=10392108
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI782370A FI65621C (fi) | 1977-09-05 | 1978-08-01 | Foerfarande foer framstaellning av som cns-aktiva medel anvaendbara 2-(4,4-difluorfenyl-butyl)-6h-oktahydropyrazino-(1,2-c) pyrimidin-6-oner |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4183933A (da) |
| JP (1) | JPS5452097A (da) |
| AT (1) | AT364365B (da) |
| BE (1) | BE870227A (da) |
| CA (1) | CA1102323A (da) |
| CH (1) | CH637133A5 (da) |
| DE (1) | DE2837089A1 (da) |
| DK (1) | DK149365C (da) |
| ES (1) | ES473070A1 (da) |
| FI (1) | FI65621C (da) |
| FR (1) | FR2401923A1 (da) |
| IT (1) | IT1159108B (da) |
| LU (1) | LU80192A1 (da) |
| MX (1) | MX5281E (da) |
| NL (1) | NL7809016A (da) |
| NO (1) | NO154194C (da) |
| SE (1) | SE442115B (da) |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3560503A (en) * | 1968-09-18 | 1971-02-02 | Council Scient Ind Res | Di-lower alkyl-substituted octahydropyrazinopyrimidinones |
| US3752816A (en) * | 1969-06-10 | 1973-08-14 | Sherwin Williams Co | Certain 3-substituted-pyrido(3,2-d)pyrimidine 2,4-(1h,3h)-diones |
| GB1284582A (en) * | 1969-11-10 | 1972-08-09 | Council Scient Ind Res | Substituted piperazinopyrimidinones |
| FR2103465A1 (en) * | 1970-08-24 | 1972-04-14 | Hokuriku Pharmaceutical | Benzhydril-pyridodiazepines - as antihistaminics and anticholinergics from dihaloalkylpiperidines and arylalkylamines with condensing agent |
| US3965257A (en) * | 1972-01-28 | 1976-06-22 | Richardson-Merrell Inc. | Compositions and methods for the treatment of the symptoms of histamine induced allergic reactions |
| US3922275A (en) * | 1972-11-09 | 1975-11-25 | Hisamitsu Pharmaceutical Co | Pyrido{8 2,3-D{9 {0 pyrimidine-2,4(1H,3H)-diones |
| DE2523730A1 (de) * | 1974-06-12 | 1976-02-12 | Hisamitsu Pharmaceutical Co | Pyrido eckige klammer auf 2,3-d eckige klammer zu pyrimidinonen |
-
1978
- 1978-08-01 FI FI782370A patent/FI65621C/fi not_active IP Right Cessation
- 1978-08-24 CH CH895178A patent/CH637133A5/de not_active IP Right Cessation
- 1978-08-24 DE DE19782837089 patent/DE2837089A1/de not_active Ceased
- 1978-08-29 IT IT27103/78A patent/IT1159108B/it active
- 1978-08-29 CA CA310,224A patent/CA1102323A/en not_active Expired
- 1978-08-30 US US05/938,041 patent/US4183933A/en not_active Expired - Lifetime
- 1978-08-31 JP JP10699678A patent/JPS5452097A/ja active Granted
- 1978-08-31 FR FR7825234A patent/FR2401923A1/fr active Granted
- 1978-09-01 NL NL7809016A patent/NL7809016A/xx not_active Application Discontinuation
- 1978-09-01 DK DK386778A patent/DK149365C/da not_active IP Right Cessation
- 1978-09-01 NO NO782995A patent/NO154194C/no unknown
- 1978-09-04 AT AT0638178A patent/AT364365B/de not_active IP Right Cessation
- 1978-09-04 MX MX787370U patent/MX5281E/es unknown
- 1978-09-04 SE SE7809288A patent/SE442115B/sv not_active IP Right Cessation
- 1978-09-05 ES ES473070A patent/ES473070A1/es not_active Expired
- 1978-09-05 BE BE190275A patent/BE870227A/xx not_active IP Right Cessation
- 1978-09-05 LU LU80192A patent/LU80192A1/de unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5452097A (en) | 1979-04-24 |
| DK149365C (da) | 1986-11-24 |
| SE442115B (sv) | 1985-12-02 |
| BE870227A (fr) | 1979-03-05 |
| ES473070A1 (es) | 1979-04-01 |
| LU80192A1 (de) | 1979-06-01 |
| DE2837089A1 (de) | 1979-03-22 |
| DK149365B (da) | 1986-05-20 |
| SE7809288L (sv) | 1979-03-06 |
| MX5281E (es) | 1983-06-02 |
| ATA638178A (de) | 1981-03-15 |
| FI65621B (fi) | 1984-02-29 |
| NO154194C (no) | 1986-08-06 |
| AT364365B (de) | 1981-10-12 |
| NO154194B (no) | 1986-04-28 |
| FI782370A7 (fi) | 1979-03-06 |
| NL7809016A (nl) | 1979-03-07 |
| DK386778A (da) | 1979-03-06 |
| FR2401923A1 (fr) | 1979-03-30 |
| CA1102323A (en) | 1981-06-02 |
| JPS5725555B2 (da) | 1982-05-29 |
| FR2401923B1 (da) | 1982-05-14 |
| IT7827103A0 (it) | 1978-08-29 |
| NO782995L (no) | 1979-03-06 |
| CH637133A5 (de) | 1983-07-15 |
| IT1159108B (it) | 1987-02-25 |
| US4183933A (en) | 1980-01-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: AB FERROSAN |