SU1187722A3 - Способ получени производных бензо - @ - триазина - Google Patents
Способ получени производных бензо - @ - триазина Download PDFInfo
- Publication number
- SU1187722A3 SU1187722A3 SU802902200A SU2902200A SU1187722A3 SU 1187722 A3 SU1187722 A3 SU 1187722A3 SU 802902200 A SU802902200 A SU 802902200A SU 2902200 A SU2902200 A SU 2902200A SU 1187722 A3 SU1187722 A3 SU 1187722A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- group
- hydrogen
- benzo
- triazine
- alkyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- GDAXJBDYNVDMDF-UHFFFAOYSA-N 1,2,4-benzotriazine Chemical compound N1=NC=NC2=CC=CC=C21 GDAXJBDYNVDMDF-UHFFFAOYSA-N 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 31
- 239000001257 hydrogen Substances 0.000 claims abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract description 3
- 239000002253 acid Substances 0.000 claims abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 6
- 230000000202 analgesic effect Effects 0.000 abstract description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 4
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- -1 pyrazinylcarbonyl Chemical group 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
- 208000010513 Stupor Diseases 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000003282 alkyl amino group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 239000002260 anti-inflammatory agent Substances 0.000 abstract 1
- 230000001741 anti-phlogistic effect Effects 0.000 abstract 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 1
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 abstract 1
- 125000003226 pyrazolyl group Chemical group 0.000 abstract 1
- 125000005400 pyridylcarbonyl group Chemical group N1=C(C=CC=C1)C(=O)* 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000003396 thiol group Chemical group [H]S* 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
- 238000002360 preparation method Methods 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 5
- 238000001819 mass spectrum Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000003110 anti-inflammatory effect Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
- 239000012346 acetyl chloride Substances 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 2
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- NPPQSCRMBWNHMW-UHFFFAOYSA-N Meprobamate Chemical compound NC(=O)OCC(C)(CCC)COC(N)=O NPPQSCRMBWNHMW-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- UYXAWHWODHRRMR-UHFFFAOYSA-N hexobarbital Chemical compound O=C1N(C)C(=O)NC(=O)C1(C)C1=CCCCC1 UYXAWHWODHRRMR-UHFFFAOYSA-N 0.000 description 1
- 229960002456 hexobarbital Drugs 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 210000003141 lower extremity Anatomy 0.000 description 1
- 229960004815 meprobamate Drugs 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229960005489 paracetamol Drugs 0.000 description 1
- 230000008855 peristalsis Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229960002895 phenylbutazone Drugs 0.000 description 1
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 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
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- A61P23/00—Anaesthetics
-
- 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]
-
- 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
- C07D487/12—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 three hetero rings
- C07D487/14—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Anesthesiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU79EE2646A HU179158B (en) | 1979-04-11 | 1979-04-11 | Process for producing triasolo-benzo-asimetrical-triasine derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU1187722A3 true SU1187722A3 (ru) | 1985-10-23 |
Family
ID=10995838
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU802902200A SU1187722A3 (ru) | 1979-04-11 | 1980-04-03 | Способ получени производных бензо - @ - триазина |
| SU823393298A SU1234401A1 (ru) | 1979-04-11 | 1982-02-18 | Производные бензо-aS-триазина,про вл ющие усиливающее наркоз действие |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU823393298A SU1234401A1 (ru) | 1979-04-11 | 1982-02-18 | Производные бензо-aS-триазина,про вл ющие усиливающее наркоз действие |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4316022A (enExample) |
| AT (1) | AT380255B (enExample) |
| AU (1) | AU534271B2 (enExample) |
| BE (1) | BE882675A (enExample) |
| CH (1) | CH644125A5 (enExample) |
| DD (1) | DD150061A5 (enExample) |
| DE (1) | DE3014011A1 (enExample) |
| ES (1) | ES490505A0 (enExample) |
| FR (1) | FR2453861A1 (enExample) |
| GB (1) | GB2047693B (enExample) |
| GR (1) | GR68093B (enExample) |
| HU (1) | HU179158B (enExample) |
| IT (1) | IT1212412B (enExample) |
| NL (1) | NL8002120A (enExample) |
| SU (2) | SU1187722A3 (enExample) |
| YU (1) | YU100180A (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5624925A (en) | 1986-09-25 | 1997-04-29 | Sri International | 1,2,4-benzotriazine oxides as radiosensitizers and selective cytotoxic agents |
| US5175287A (en) * | 1986-09-25 | 1992-12-29 | S R I International | Process for preparing 1,2,4-benzotriazine oxides |
| WO2000034278A1 (en) * | 1998-12-04 | 2000-06-15 | Toray Industries, Inc. | Triazolo derivatives and chemokine inhibitors containing the same as the active ingredient |
| US6833454B1 (en) | 2003-01-15 | 2004-12-21 | The United States Of America As Represented By The Secretary Of The Navy | Chemical compounds containing bis(triazolo)triazine structures and methods thereof |
| EP1502918A1 (en) * | 2003-07-31 | 2005-02-02 | Bayer CropScience GmbH | The use of fused ring-1,2,4-benzotriazine derivatives as herbicides or plant growth regulators for the control of undesired plants or vegetation, compounds and compositions thereof, and processes for their preparation |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3933816A (en) * | 1974-09-12 | 1976-01-20 | The Upjohn Company | 3-(Substituted aminomethyl)-7-substituted-3,5-dihydro-as-triazino[4,3-a][1,5]benzodiazepines |
| US4017492A (en) * | 1976-04-02 | 1977-04-12 | The Upjohn Company | As-triazinobenzodiazepin-1-ones |
-
1979
- 1979-04-11 HU HU79EE2646A patent/HU179158B/hu not_active IP Right Cessation
-
1980
- 1980-03-28 US US06/135,143 patent/US4316022A/en not_active Expired - Lifetime
- 1980-03-31 GB GB8010792A patent/GB2047693B/en not_active Expired
- 1980-04-02 GR GR61603A patent/GR68093B/el unknown
- 1980-04-03 SU SU802902200A patent/SU1187722A3/ru active
- 1980-04-08 BE BE1/9779A patent/BE882675A/fr not_active IP Right Cessation
- 1980-04-08 DD DD80220282A patent/DD150061A5/de unknown
- 1980-04-10 IT IT8021284A patent/IT1212412B/it active
- 1980-04-10 AU AU57301/80A patent/AU534271B2/en not_active Ceased
- 1980-04-10 FR FR8008051A patent/FR2453861A1/fr active Granted
- 1980-04-10 CH CH274180A patent/CH644125A5/de not_active IP Right Cessation
- 1980-04-11 AT AT0197380A patent/AT380255B/de not_active IP Right Cessation
- 1980-04-11 ES ES490505A patent/ES490505A0/es active Granted
- 1980-04-11 YU YU01001/80A patent/YU100180A/xx unknown
- 1980-04-11 NL NL8002120A patent/NL8002120A/nl not_active Application Discontinuation
- 1980-04-11 DE DE19803014011 patent/DE3014011A1/de not_active Withdrawn
-
1982
- 1982-02-18 SU SU823393298A patent/SU1234401A1/ru active
Non-Patent Citations (1)
| Title |
|---|
| Вейганд-Хильгетаг. Методы эксперимейта в органической химии. М.: Хими , 1968, с. 431-432, 450-451. Патент СССР № 888823, кл. С 07 D 471/04, 1975. * |
Also Published As
| Publication number | Publication date |
|---|---|
| YU100180A (en) | 1983-09-30 |
| ES8104807A1 (es) | 1981-04-16 |
| AU534271B2 (en) | 1984-01-12 |
| AT380255B (de) | 1986-05-12 |
| IT1212412B (it) | 1989-11-22 |
| SU1234401A1 (ru) | 1986-05-30 |
| AU5730180A (en) | 1980-10-16 |
| FR2453861B1 (enExample) | 1983-06-24 |
| GR68093B (enExample) | 1981-10-30 |
| IT8021284A0 (it) | 1980-04-10 |
| ES490505A0 (es) | 1981-04-16 |
| NL8002120A (nl) | 1980-10-14 |
| BE882675A (fr) | 1980-10-08 |
| GB2047693B (en) | 1983-05-25 |
| GB2047693A (en) | 1980-12-03 |
| HU179158B (en) | 1982-08-28 |
| FR2453861A1 (fr) | 1980-11-07 |
| US4316022A (en) | 1982-02-16 |
| CH644125A5 (de) | 1984-07-13 |
| ATA197380A (de) | 1985-09-15 |
| DE3014011A1 (de) | 1980-11-27 |
| DD150061A5 (de) | 1981-08-12 |
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