DK142456B - Analogifremgangsmåde til fremstilling af 1,4-benzodiazepinderivater eller salte deraf. - Google Patents
Analogifremgangsmåde til fremstilling af 1,4-benzodiazepinderivater eller salte deraf. Download PDFInfo
- Publication number
- DK142456B DK142456B DK247869AA DK247869A DK142456B DK 142456 B DK142456 B DK 142456B DK 247869A A DK247869A A DK 247869AA DK 247869 A DK247869 A DK 247869A DK 142456 B DK142456 B DK 142456B
- Authority
- DK
- Denmark
- Prior art keywords
- acid
- residue
- solution
- dihydro
- fluorophenyl
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims description 15
- 238000000034 method Methods 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 5
- GUJAGMICFDYKNR-UHFFFAOYSA-N 1,4-benzodiazepine Chemical class N1C=CN=CC2=CC=CC=C12 GUJAGMICFDYKNR-UHFFFAOYSA-N 0.000 title claims description 4
- 239000002253 acid Substances 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims description 7
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 5
- 125000005400 pyridylcarbonyl group Chemical group N1=C(C=CC=C1)C(=O)* 0.000 claims description 5
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 4
- 125000001589 carboacyl group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims 4
- 125000004429 atom Chemical group 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 80
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
- 239000000243 solution Substances 0.000 description 50
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 39
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 34
- -1 isopropylcarbonyl Chemical group 0.000 description 33
- 239000000203 mixture Substances 0.000 description 26
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 18
- 239000003921 oil Substances 0.000 description 18
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 16
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 11
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- 239000000047 product Substances 0.000 description 10
- FOCBRQQHNOKOJQ-UHFFFAOYSA-N 7-chloro-5-(2-fluorophenyl)-1-(2-hydroxyethyl)-3h-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(CCO)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1F FOCBRQQHNOKOJQ-UHFFFAOYSA-N 0.000 description 9
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- 238000003756 stirring Methods 0.000 description 6
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- 230000002378 acidificating effect Effects 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
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- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 4
- 229940014800 succinic anhydride Drugs 0.000 description 4
- FTEZJSXSARPZHJ-UHFFFAOYSA-N 2-methoxypyridine-3-carboxylic acid Chemical compound COC1=NC=CC=C1C(O)=O FTEZJSXSARPZHJ-UHFFFAOYSA-N 0.000 description 3
- FQIUCPGDKPXSLL-UHFFFAOYSA-N 5-bromopyridine-3-carboxylic acid Chemical compound OC(=O)C1=CN=CC(Br)=C1 FQIUCPGDKPXSLL-UHFFFAOYSA-N 0.000 description 3
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- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 description 2
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- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical group 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000004816 paper chromatography Methods 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- RVQZKNOMKUSGCI-UHFFFAOYSA-N pyridine-4-carbonyl chloride Chemical compound ClC(=O)C1=CC=NC=C1 RVQZKNOMKUSGCI-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229940125723 sedative agent Drugs 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 230000001225 therapeutic effect 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK91172A DK143900C (da) | 1969-03-12 | 1972-02-28 | Analogifremgangsmaade til fremstilling af 1,4-benzodiazepinderivater eller salte deraf |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US72735668A | 1968-05-07 | 1968-05-07 | |
| US72735668 | 1968-05-07 | ||
| US80670269A | 1969-03-12 | 1969-03-12 | |
| US80670269 | 1969-03-12 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DK142456B true DK142456B (da) | 1980-11-03 |
| DK142456C DK142456C (ja) | 1981-08-03 |
Family
ID=27111492
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK247869AA DK142456B (da) | 1968-05-07 | 1969-05-06 | Analogifremgangsmåde til fremstilling af 1,4-benzodiazepinderivater eller salte deraf. |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPS4810479B1 (ja) |
| AT (2) | AT288403B (ja) |
| BE (1) | BE732558A (ja) |
| CA (2) | CA971170A (ja) |
| CH (3) | CH579058A5 (ja) |
| DE (1) | DE1923139C2 (ja) |
| DK (1) | DK142456B (ja) |
| FR (1) | FR2007970A1 (ja) |
| GB (1) | GB1208541A (ja) |
| IL (1) | IL32100A (ja) |
| MY (1) | MY7100097A (ja) |
| NL (1) | NL165176C (ja) |
| NO (1) | NO123492B (ja) |
| SE (1) | SE351647B (ja) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6038255U (ja) * | 1983-08-24 | 1985-03-16 | 丸山 久子 | 簡易ふくさ |
| US7029918B2 (en) | 2002-01-25 | 2006-04-18 | Roche Diagnostics Operations, Inc. | Water-soluble derivatives of lipophilic drugs |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT224121B (de) * | 1959-12-10 | 1962-11-12 | Hoffmann La Roche | Verfahren zur Herstellung von neuen 1,4-Benzodiazepin-Derivaten |
| AT256114B (de) * | 1964-08-13 | 1967-08-10 | Hoffmann La Roche | Verfahren zur Herstellung von neuen Benzodiazepinderivaten |
-
1969
- 1969-04-25 CH CH1581271A patent/CH579058A5/xx not_active IP Right Cessation
- 1969-04-25 CA CA049,759A patent/CA971170A/en not_active Expired
- 1969-04-25 CH CH631569A patent/CH568996A5/xx not_active IP Right Cessation
- 1969-04-25 CH CH1581371A patent/CH579059A5/xx not_active IP Right Cessation
- 1969-04-29 IL IL32100A patent/IL32100A/en unknown
- 1969-05-01 CA CA050,258,A patent/CA950455A/en not_active Expired
- 1969-05-05 GB GB22780/69A patent/GB1208541A/en not_active Expired
- 1969-05-06 DK DK247869AA patent/DK142456B/da not_active IP Right Cessation
- 1969-05-06 AT AT434369A patent/AT288403B/de not_active IP Right Cessation
- 1969-05-06 NO NO1865/69A patent/NO123492B/no unknown
- 1969-05-06 FR FR6914421A patent/FR2007970A1/fr not_active Withdrawn
- 1969-05-06 BE BE732558D patent/BE732558A/xx not_active IP Right Cessation
- 1969-05-06 AT AT434469A patent/AT288404B/de not_active IP Right Cessation
- 1969-05-07 SE SE06468/69A patent/SE351647B/xx unknown
- 1969-05-07 NL NL6906971.A patent/NL165176C/xx not_active IP Right Cessation
- 1969-05-07 DE DE1923139A patent/DE1923139C2/de not_active Expired
- 1969-05-07 JP JP44035117A patent/JPS4810479B1/ja active Pending
-
1971
- 1971-12-30 MY MY97/71A patent/MY7100097A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1208541A (en) | 1970-10-14 |
| NL165176B (nl) | 1980-10-15 |
| NL165176C (nl) | 1981-03-16 |
| DE1923139C2 (de) | 1982-04-15 |
| IL32100A (en) | 1972-12-29 |
| SE351647B (ja) | 1972-12-04 |
| NL6906971A (ja) | 1969-11-11 |
| DE1923139A1 (de) | 1969-11-20 |
| CA950455A (en) | 1974-07-02 |
| JPS4810479B1 (ja) | 1973-04-03 |
| CA971170A (en) | 1975-07-15 |
| CH579059A5 (ja) | 1976-08-31 |
| MY7100097A (en) | 1971-12-31 |
| BE732558A (ja) | 1969-11-06 |
| AT288403B (de) | 1971-03-10 |
| FR2007970A1 (ja) | 1970-01-16 |
| CH579058A5 (ja) | 1976-08-31 |
| IL32100A0 (en) | 1969-06-25 |
| CH568996A5 (ja) | 1975-11-14 |
| NO123492B (ja) | 1971-11-29 |
| DK142456C (ja) | 1981-08-03 |
| AT288404B (de) | 1971-03-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PBP | Patent lapsed |