DE1645959A1 - Heterocyclische Verbindungen,Verfahren zu ihrer Herstellung und deren Verwendung - Google Patents
Heterocyclische Verbindungen,Verfahren zu ihrer Herstellung und deren VerwendungInfo
- Publication number
- DE1645959A1 DE1645959A1 DE19641645959 DE1645959A DE1645959A1 DE 1645959 A1 DE1645959 A1 DE 1645959A1 DE 19641645959 DE19641645959 DE 19641645959 DE 1645959 A DE1645959 A DE 1645959A DE 1645959 A1 DE1645959 A1 DE 1645959A1
- Authority
- DE
- Germany
- Prior art keywords
- product
- alkyl
- acid
- melting point
- ring
- 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 10
- 150000002391 heterocyclic compounds Chemical class 0.000 title claims 2
- 238000002360 preparation method Methods 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 24
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 20
- 239000005711 Benzoic acid Substances 0.000 claims description 12
- -1 aminohalophenyl Chemical group 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 235000010233 benzoic acid Nutrition 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 150000004985 diamines Chemical class 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000000217 alkyl group Chemical group 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
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims description 4
- 150000004715 keto acids Chemical class 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims description 2
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000005059 halophenyl group Chemical group 0.000 claims 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims 1
- 239000000047 product Substances 0.000 description 67
- 238000002844 melting Methods 0.000 description 40
- 230000008018 melting Effects 0.000 description 40
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 32
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- 238000001953 recrystallisation Methods 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 14
- 238000004458 analytical method Methods 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- FGTYTUFKXYPTML-UHFFFAOYSA-N 2-benzoylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 FGTYTUFKXYPTML-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 230000001410 anti-tremor Effects 0.000 description 6
- 239000005457 ice water Substances 0.000 description 6
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 6
- 230000001773 anti-convulsant effect Effects 0.000 description 5
- 239000001961 anticonvulsive agent Substances 0.000 description 5
- 229960003965 antiepileptics Drugs 0.000 description 5
- UYBWIEGTWASWSR-UHFFFAOYSA-N 1,3-diaminopropan-2-ol Chemical compound NCC(O)CN UYBWIEGTWASWSR-UHFFFAOYSA-N 0.000 description 4
- 230000001430 anti-depressive effect Effects 0.000 description 4
- 239000000935 antidepressant agent Substances 0.000 description 4
- 229940005513 antidepressants Drugs 0.000 description 4
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 3
- DRZDPLDMEHBZDN-UHFFFAOYSA-N 2,3-dihydroisoindol-5-one Chemical compound O=C1C=CC2=CNCC2=C1 DRZDPLDMEHBZDN-UHFFFAOYSA-N 0.000 description 2
- NJXDTGLUPRKMFN-UHFFFAOYSA-N 2-(2-phenylacetyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)CC1=CC=CC=C1 NJXDTGLUPRKMFN-UHFFFAOYSA-N 0.000 description 2
- MQECGSWGDQIHHD-UHFFFAOYSA-N 2-(3-amino-4-chlorobenzoyl)benzoic acid Chemical compound C1=C(Cl)C(N)=CC(C(=O)C=2C(=CC=CC=2)C(O)=O)=C1 MQECGSWGDQIHHD-UHFFFAOYSA-N 0.000 description 2
- FLPQLUGZLPSVOG-UHFFFAOYSA-N 2-benzoylcyclohexane-1-carboxylic acid Chemical compound OC(=O)C1CCCCC1C(=O)C1=CC=CC=C1 FLPQLUGZLPSVOG-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 230000002082 anti-convulsion Effects 0.000 description 2
- GHWVXCQZPNWFRO-UHFFFAOYSA-N butane-2,3-diamine Chemical compound CC(N)C(C)N GHWVXCQZPNWFRO-UHFFFAOYSA-N 0.000 description 2
- 230000002920 convulsive effect Effects 0.000 description 2
- 230000003001 depressive effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- YWECCEXWKFHHQJ-UHFFFAOYSA-N 2-(4-chlorobenzoyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)C1=CC=C(Cl)C=C1 YWECCEXWKFHHQJ-UHFFFAOYSA-N 0.000 description 1
- KPJANWLDEVDGEA-UHFFFAOYSA-N 2-(thiophene-2-carbonyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)C1=CC=CS1 KPJANWLDEVDGEA-UHFFFAOYSA-N 0.000 description 1
- QDAWXRKTSATEOP-UHFFFAOYSA-N 2-acetylbenzoic acid Chemical compound CC(=O)C1=CC=CC=C1C(O)=O QDAWXRKTSATEOP-UHFFFAOYSA-N 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 description 1
- SNQJWBJIHWHILY-UHFFFAOYSA-N 3-benzyl-3-hydroxy-2-benzofuran-1-one Chemical compound O1C(=O)C2=CC=CC=C2C1(O)CC1=CC=CC=C1 SNQJWBJIHWHILY-UHFFFAOYSA-N 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- JJALHZDTTJJYCI-UHFFFAOYSA-N 6-benzoylcyclohex-3-ene-1-carboxylic acid Chemical compound OC(=O)C1CC=CCC1C(=O)C1=CC=CC=C1 JJALHZDTTJJYCI-UHFFFAOYSA-N 0.000 description 1
- VHOLDVWNAVAZQQ-UHFFFAOYSA-N 9b-phenyl-2,3-dihydro-1h-imidazo[2,1-a]isoindol-5-one Chemical compound C12=CC=CC=C2C(=O)N2CCNC21C1=CC=CC=C1 VHOLDVWNAVAZQQ-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- QKDLQFSLLCQTOH-UHFFFAOYSA-N Trichodonin Natural products C1C(O)C2C3(COC(=O)C)C(C=O)C(C)(C)CCC3OC(=O)C22C(=O)C(=C)C1C2 QKDLQFSLLCQTOH-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- CHCVONSEJKYYBG-UHFFFAOYSA-N indol-5-one Chemical compound O=C1C=CC2=NC=CC2=C1 CHCVONSEJKYYBG-UHFFFAOYSA-N 0.000 description 1
- SOWOYMBNJVLWGP-UHFFFAOYSA-N isoindol-5-one Chemical compound O=C1C=CC2=CN=CC2=C1 SOWOYMBNJVLWGP-UHFFFAOYSA-N 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- KFIGICHILYTCJF-UHFFFAOYSA-N n'-methylethane-1,2-diamine Chemical compound CNCCN KFIGICHILYTCJF-UHFFFAOYSA-N 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
- 239000006186 oral dosage form Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000006201 parenteral dosage form Substances 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 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
- 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
- A61K31/00—Medicinal preparations containing organic active ingredients
-
- 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
- C07D471/12—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 three hetero rings
- C07D471/14—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US27221663A | 1963-04-11 | 1963-04-11 | |
| US33661564A | 1964-01-09 | 1964-01-09 | |
| US33662564A | 1964-01-09 | 1964-01-09 | |
| US52393066A | 1966-02-01 | 1966-02-01 | |
| US523955A US3311629A (en) | 1963-04-11 | 1966-02-01 | 9b-aryl-1, 2, 3, 9b-tetrahydro-5h-imidazo[1, 2-a] pyrido[3, 2-c]pyrrol-5-ones and related compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1645959A1 true DE1645959A1 (de) | 1970-09-10 |
Family
ID=27540561
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19641645959 Pending DE1645959A1 (de) | 1963-04-11 | 1964-04-09 | Heterocyclische Verbindungen,Verfahren zu ihrer Herstellung und deren Verwendung |
| DE19681445443 Pending DE1445443A1 (de) | 1963-04-11 | 1968-11-20 | Verfahren zur Herstellung von Benzodiazocin-Verbindungen |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19681445443 Pending DE1445443A1 (de) | 1963-04-11 | 1968-11-20 | Verfahren zur Herstellung von Benzodiazocin-Verbindungen |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US3311629A (enExample) |
| BE (1) | BE646221A (enExample) |
| BR (1) | BR6458056D0 (enExample) |
| CH (2) | CH464216A (enExample) |
| DE (2) | DE1645959A1 (enExample) |
| DK (1) | DK117636B (enExample) |
| FR (1) | FR3434M (enExample) |
| GB (2) | GB1059174A (enExample) |
| NL (2) | NL6403794A (enExample) |
| SE (1) | SE310885B (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3994920A (en) * | 1963-04-11 | 1976-11-30 | American Home Products Corporation | 5H-imidazo[2,1-a]isoindol-5-one compounds |
| JPH06505017A (ja) * | 1991-02-28 | 1994-06-09 | ベーリンガー マンハイム ゲーエムベーハー | 三環式イソインドリノンの抗ウイルス医薬としての使用、ならびに新規な光学活性イソインドリノン |
| CA2551178C (en) * | 2003-12-24 | 2012-11-06 | Biota Scientific Management Pty Ltd | Polycyclic agents for the treatment of respiratory syncytial virus infections |
| TWI423972B (zh) | 2006-09-28 | 2014-01-21 | Biota Scient Management | 治療呼吸系融合細胞病毒感染之多環劑 |
| TWI508968B (zh) | 2010-02-08 | 2015-11-21 | Biota Scient Management | 用於治療呼吸道融合性病毒感染的化合物 |
| US8796303B2 (en) | 2010-11-26 | 2014-08-05 | Biota Scientific Management Pty Ltd. | Imidazo[2,1-G][1,7]naphthyridines for treating respiratory syncytial virus infections |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3108108A (en) * | 1959-09-25 | 1963-10-22 | Bayer Ag | Aza analogues of polynuclear o-quinones |
-
0
- NL NL137586D patent/NL137586C/xx active
-
1964
- 1964-04-02 BR BR158056/64A patent/BR6458056D0/pt unknown
- 1964-04-07 BE BE646221D patent/BE646221A/xx unknown
- 1964-04-09 DE DE19641645959 patent/DE1645959A1/de active Pending
- 1964-04-09 NL NL6403794A patent/NL6403794A/xx unknown
- 1964-04-09 DK DK177864AA patent/DK117636B/da unknown
- 1964-04-10 GB GB14837/64A patent/GB1059174A/en not_active Expired
- 1964-04-10 GB GB11917/66A patent/GB1059175A/en not_active Expired
- 1964-04-10 CH CH467364A patent/CH464216A/de unknown
- 1964-04-10 SE SE4494/64A patent/SE310885B/xx unknown
- 1964-04-10 CH CH893066A patent/CH465623A/de unknown
- 1964-06-03 FR FR976949A patent/FR3434M/fr active Active
-
1966
- 1966-02-01 US US523955A patent/US3311629A/en not_active Expired - Lifetime
- 1966-02-01 US US523930A patent/US3423421A/en not_active Expired - Lifetime
-
1968
- 1968-11-20 DE DE19681445443 patent/DE1445443A1/de active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DK117636B (da) | 1970-05-19 |
| GB1059175A (en) | 1967-02-15 |
| CH464216A (de) | 1968-10-31 |
| US3423421A (en) | 1969-01-21 |
| US3311629A (en) | 1967-03-28 |
| CH465623A (de) | 1968-11-30 |
| BE646221A (enExample) | 1964-10-07 |
| BR6458056D0 (pt) | 1973-08-02 |
| NL6403794A (enExample) | 1964-10-12 |
| NL137586C (enExample) | |
| SE310885B (enExample) | 1969-05-19 |
| DE1445443A1 (de) | 1968-11-21 |
| GB1059174A (en) | 1967-02-15 |
| FR3434M (fr) | 1964-07-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHN | Withdrawal |