NO132098B - - Google Patents
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- Publication number
- NO132098B NO132098B NO154771A NO154771A NO132098B NO 132098 B NO132098 B NO 132098B NO 154771 A NO154771 A NO 154771A NO 154771 A NO154771 A NO 154771A NO 132098 B NO132098 B NO 132098B
- Authority
- NO
- Norway
- Prior art keywords
- formula
- hydroxy
- acid
- phenyl
- chlorophenyl
- Prior art date
Links
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 17
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 6
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 239000012458 free base Substances 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- 238000002844 melting Methods 0.000 description 14
- 230000008018 melting Effects 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 7
- 238000001953 recrystallisation Methods 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 5
- PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical compound C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- -1 tri(C 4 )alkylamine Chemical class 0.000 description 4
- WUSKUMDOLSBRHW-UHFFFAOYSA-N 2-(4-chlorobenzoyl)benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1C(=O)C1=CC=C(Cl)C=C1 WUSKUMDOLSBRHW-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- JATMCAQQSXISOR-UHFFFAOYSA-N n-(2-aminoethyl)-4-methylbenzenesulfonamide Chemical compound CC1=CC=C(S(=O)(=O)NCCN)C=C1 JATMCAQQSXISOR-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- UVNXNSUKKOLFBM-UHFFFAOYSA-N imidazo[2,1-b][1,3,4]thiadiazole Chemical compound N1=CSC2=NC=CN21 UVNXNSUKKOLFBM-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical group CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- GJJVTLOHDLKVFS-UHFFFAOYSA-N 2-benzoylbenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 GJJVTLOHDLKVFS-UHFFFAOYSA-N 0.000 description 1
- NRGGMCIBEHEAIL-UHFFFAOYSA-N 2-ethylpyridine Chemical compound CCC1=CC=CC=N1 NRGGMCIBEHEAIL-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- BJTHOLRDMKDSNE-UHFFFAOYSA-N FC=1C=C(C(=O)C2=C(C(=O)Cl)C=CC=C2)C=CC=1 Chemical compound FC=1C=C(C(=O)C2=C(C(=O)Cl)C=CC=C2)C=CC=1 BJTHOLRDMKDSNE-UHFFFAOYSA-N 0.000 description 1
- ZPXSCAKFGYXMGA-UHFFFAOYSA-N Mazindol Chemical compound N12CCN=C2C2=CC=CC=C2C1(O)C1=CC=C(Cl)C=C1 ZPXSCAKFGYXMGA-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 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
- 239000003513 alkali Substances 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 208000022531 anorexia Diseases 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 206010061428 decreased appetite Diseases 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 150000002518 isoindoles Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- VMIKHXOZRYCZSG-UHFFFAOYSA-N n-(2-aminoethyl)-3,4-dimethylbenzenesulfonamide Chemical compound CC1=CC=C(S(=O)(=O)NCCN)C=C1C VMIKHXOZRYCZSG-UHFFFAOYSA-N 0.000 description 1
- MWEBCGQFQBAAJP-UHFFFAOYSA-N n-(2-aminoethyl)-4-chlorobenzenesulfonamide Chemical compound NCCNS(=O)(=O)C1=CC=C(Cl)C=C1 MWEBCGQFQBAAJP-UHFFFAOYSA-N 0.000 description 1
- JVFJSUCEQDCCAH-UHFFFAOYSA-N n-(2-aminoethyl)benzenesulfonamide Chemical compound NCCNS(=O)(=O)C1=CC=CC=C1 JVFJSUCEQDCCAH-UHFFFAOYSA-N 0.000 description 1
- GCDZDXVTDCMNMN-UHFFFAOYSA-N n-(2-aminoethyl)methanesulfonamide Chemical compound CS(=O)(=O)NCCN GCDZDXVTDCMNMN-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229960001407 sodium bicarbonate Drugs 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000015961 tonic Nutrition 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- 229960000716 tonics Drugs 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US3277270A | 1970-04-28 | 1970-04-28 | |
| US9250370A | 1970-11-24 | 1970-11-24 | |
| US11588471A | 1971-02-16 | 1971-02-16 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO132098B true NO132098B (es) | 1975-06-09 |
| NO132098C NO132098C (es) | 1975-09-17 |
Family
ID=27364216
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO154771A NO132098C (es) | 1970-04-28 | 1971-04-26 |
Country Status (14)
| Country | Link |
|---|---|
| AT (1) | AT323729B (es) |
| BE (1) | BE766294A (es) |
| CA (1) | CA952114A (es) |
| CH (1) | CH548406A (es) |
| CS (1) | CS181208B2 (es) |
| DD (1) | DD96944A5 (es) |
| DE (1) | DE2120263A1 (es) |
| ES (2) | ES390610A1 (es) |
| FI (1) | FI52727C (es) |
| FR (2) | FR2086411B1 (es) |
| GB (1) | GB1355074A (es) |
| NL (1) | NL7105665A (es) |
| NO (1) | NO132098C (es) |
| YU (1) | YU34697B (es) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3454592A (en) * | 1963-12-18 | 1969-07-08 | Sandoz Ag | 2-(omega-hydroxyalkyl)-3-hydroxy-3-phenylisoindolones |
-
1971
- 1971-03-26 YU YU103671A patent/YU34697B/xx unknown
- 1971-04-16 CH CH556071A patent/CH548406A/xx not_active IP Right Cessation
- 1971-04-26 FR FR7114732A patent/FR2086411B1/fr not_active Expired
- 1971-04-26 ES ES390610A patent/ES390610A1/es not_active Expired
- 1971-04-26 BE BE766294A patent/BE766294A/xx unknown
- 1971-04-26 DE DE19712120263 patent/DE2120263A1/de active Pending
- 1971-04-26 NO NO154771A patent/NO132098C/no unknown
- 1971-04-26 GB GB1133471A patent/GB1355074A/en not_active Expired
- 1971-04-26 CA CA111,339A patent/CA952114A/en not_active Expired
- 1971-04-27 AT AT362571A patent/AT323729B/de not_active IP Right Cessation
- 1971-04-27 FI FI116671A patent/FI52727C/fi active
- 1971-04-27 NL NL7105665A patent/NL7105665A/xx unknown
- 1971-04-27 CS CS303571A patent/CS181208B2/cs unknown
- 1971-04-27 DD DD16168971A patent/DD96944A5/xx unknown
-
1972
- 1972-01-28 FR FR7202872A patent/FR2120188B1/fr not_active Expired
-
1973
- 1973-05-25 ES ES415167A patent/ES415167A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| SU442598A3 (ru) | 1974-09-05 |
| ES390610A1 (es) | 1974-06-16 |
| FR2120188A1 (es) | 1972-08-11 |
| NO132098C (es) | 1975-09-17 |
| ES415167A1 (es) | 1976-05-16 |
| CA952114A (en) | 1974-07-30 |
| AT323729B (de) | 1975-07-25 |
| YU103671A (en) | 1979-07-10 |
| FI52727B (es) | 1977-08-01 |
| FR2086411A1 (es) | 1971-12-31 |
| DE2120263A1 (de) | 1971-11-18 |
| DD96944A5 (es) | 1973-04-12 |
| YU34697B (en) | 1979-12-31 |
| NL7105665A (es) | 1971-11-01 |
| CS181208B2 (en) | 1978-03-31 |
| FR2120188B1 (es) | 1977-12-23 |
| BE766294A (fr) | 1971-10-26 |
| FI52727C (fi) | 1977-11-10 |
| FR2086411B1 (es) | 1973-06-08 |
| GB1355074A (en) | 1974-06-05 |
| CH548406A (de) | 1974-04-30 |
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