GB1268772A - NOVEL alpha-CARBOLINE DERIVATIVES, THE PREPARATION THEREOF AND COMPOSITIONS CONTAINING THE SAME - Google Patents
NOVEL alpha-CARBOLINE DERIVATIVES, THE PREPARATION THEREOF AND COMPOSITIONS CONTAINING THE SAMEInfo
- Publication number
- GB1268772A GB1268772A GB1273168A GB1273168A GB1268772A GB 1268772 A GB1268772 A GB 1268772A GB 1273168 A GB1273168 A GB 1273168A GB 1273168 A GB1273168 A GB 1273168A GB 1268772 A GB1268772 A GB 1268772A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compositions
- substituted
- carboline
- araliphatic
- lotions
- 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.)
- Expired
Links
- 239000000203 mixture Substances 0.000 title abstract 5
- BPMFPOGUJAAYHL-UHFFFAOYSA-N 9H-Pyrido[2,3-b]indole Chemical class C1=CC=C2C3=CC=CC=C3NC2=N1 BPMFPOGUJAAYHL-UHFFFAOYSA-N 0.000 title abstract 4
- 238000002360 preparation method Methods 0.000 title abstract 3
- 239000007788 liquid Substances 0.000 abstract 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- 125000001931 aliphatic group Chemical group 0.000 abstract 2
- 230000000840 anti-viral effect Effects 0.000 abstract 2
- -1 araliphatic Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 239000006210 lotion Substances 0.000 abstract 2
- 239000003973 paint Substances 0.000 abstract 2
- 239000000546 pharmaceutical excipient Substances 0.000 abstract 2
- 239000000843 powder Substances 0.000 abstract 2
- 241000919811 Collyria Species 0.000 abstract 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical group OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 abstract 1
- 239000004098 Tetracycline Substances 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000004442 acylamino group Chemical group 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 239000000443 aerosol Substances 0.000 abstract 1
- 125000003282 alkyl amino group Chemical group 0.000 abstract 1
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- 229940121363 anti-inflammatory agent Drugs 0.000 abstract 1
- 239000002260 anti-inflammatory agent Substances 0.000 abstract 1
- 229940088710 antibiotic agent Drugs 0.000 abstract 1
- VQODGRNSFPNSQE-DVTGEIKXSA-N betamethasone phosphate Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)COP(O)(O)=O)(O)[C@@]1(C)C[C@@H]2O VQODGRNSFPNSQE-DVTGEIKXSA-N 0.000 abstract 1
- 239000006172 buffering agent Substances 0.000 abstract 1
- 239000002775 capsule Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 229940112822 chewing gum Drugs 0.000 abstract 1
- 235000015218 chewing gum Nutrition 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 235000009508 confectionery Nutrition 0.000 abstract 1
- 239000006071 cream Substances 0.000 abstract 1
- 238000010410 dusting Methods 0.000 abstract 1
- 239000003995 emulsifying agent Substances 0.000 abstract 1
- 230000001804 emulsifying effect Effects 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 abstract 1
- 239000003889 eye drop Substances 0.000 abstract 1
- 229940012356 eye drops Drugs 0.000 abstract 1
- 239000008187 granular material Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 239000007937 lozenge Substances 0.000 abstract 1
- 239000007923 nasal drop Substances 0.000 abstract 1
- 229940100662 nasal drops Drugs 0.000 abstract 1
- 230000000701 neuroleptic effect Effects 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 239000012038 nucleophile Substances 0.000 abstract 1
- 239000002674 ointment Substances 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 239000007921 spray Substances 0.000 abstract 1
- 230000003019 stabilising effect Effects 0.000 abstract 1
- 150000003431 steroids Chemical class 0.000 abstract 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 1
- 239000000829 suppository Substances 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
- 239000006188 syrup Substances 0.000 abstract 1
- 235000020357 syrup Nutrition 0.000 abstract 1
- 239000003826 tablet Substances 0.000 abstract 1
- 229960002180 tetracycline Drugs 0.000 abstract 1
- 229930101283 tetracycline Natural products 0.000 abstract 1
- 235000019364 tetracycline Nutrition 0.000 abstract 1
- 150000003522 tetracyclines Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Medicinal Preparation (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
1,268,772. Antiviral compositions. GLAXO LABORATORIES Ltd. 14 March, 1969 [15 March, 1968(2)], Nos. 12730/68 and 12731/68. Heading A5B. [Also in Division C2] Pharmaceutical or veterinary compositions having antiviral activity comprise, as active ingredient, at least one 2-substituted α-carboline of the general formula wherein R is a hydrogen atom or a substituted or unsubstituted aliphatic. araliphatic, aromatic or acyl group, X is a halogen atom or the residue of a nucleophile and wherein the nucleus is optionally additionally substituted by hydroxy, aliphatic, araliphatic, aromatic, carboxy, carboxylic acid ester, acylamino, amino, alkylamino, acyloxy, ether, nitro or sulphonic acid groups or halogen atoms, or physiologically compatible salt thereof, together with one or more pharmaceutical or veterinary carrier or excipient and/or other medicinal agents, e.g. anti-inflammatory agents such as steroids (e.g. betamethasone-21-phosphate) or antibiotics, such as tetracycline. The compositions may be administered orally, topically, rectally, intravaginally or parenterally in the form of tablets, capsules, lozenges, chewing gum, medicated sweets, solutions, suspensions, syrups, elixirs, emulsions, granules for constitution before use, liquid sprays, powder insufflations, nasal drops or ointments, throat paints, gargles, ophthalmic preparations and collyria, skin paints, lotions, creams, dusting powders, medicated dressings, eye drops and lotions, aerosols, suppositories, pessaries or injectable preparations. The compositions may also be formulated with a solid carrier or excipient or a sterile, pyrogen-free liquid or an aqueous oily liquid containing one or more suspending, dispersing, stabilising, preserving, solubilising, emulsifying or buffering agents. The compound 2-chloro-9-(3'-dimethylaminopiopyl) - α - carboline additionally shows neuroleptic activity.
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1273168A GB1268772A (en) | 1968-03-15 | 1968-03-15 | NOVEL alpha-CARBOLINE DERIVATIVES, THE PREPARATION THEREOF AND COMPOSITIONS CONTAINING THE SAME |
| AT253169A AT304533B (en) | 1968-03-15 | 1969-03-14 | Process for the production of new α-carbolines and their salts |
| DE19691913119 DE1913119A1 (en) | 1968-03-15 | 1969-03-14 | Alpha carbolines and their method of manufacture |
| CH1876271A CH536847A (en) | 1968-03-15 | 1969-03-14 | 2 substituted x-carbolines with antiviral activity and |
| CH1876371A CH536848A (en) | 1968-03-15 | 1969-03-14 | Process for the preparation of virostatically effective new α-carbolines |
| AT736471A AT310155B (en) | 1968-03-15 | 1969-03-14 | Process for the production of new α-carbolines and their salts |
| BE729855D BE729855A (en) | 1968-03-15 | 1969-03-14 | |
| CH389969A CH553200A (en) | 1968-03-15 | 1969-03-14 | PROCESS FOR PRODUCING VIROSTATICALLY EFFECTIVE NEW (ALPHA) CARBOLINES. |
| IE33869A IE32705B1 (en) | 1968-03-15 | 1969-03-14 | Novel alpha-carboline derivatives,the preparation thereof and compositions containing the same |
| NL6903973A NL6903973A (en) | 1968-03-15 | 1969-03-14 | |
| FR6907280A FR2003999A1 (en) | 1968-03-15 | 1969-03-14 | |
| CH1271771A CH561206A5 (en) | 1968-03-15 | 1969-03-14 |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1273068 | 1968-03-15 | ||
| GB1273168A GB1268772A (en) | 1968-03-15 | 1968-03-15 | NOVEL alpha-CARBOLINE DERIVATIVES, THE PREPARATION THEREOF AND COMPOSITIONS CONTAINING THE SAME |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1268772A true GB1268772A (en) | 1972-03-29 |
Family
ID=26249226
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1273168A Expired GB1268772A (en) | 1968-03-15 | 1968-03-15 | NOVEL alpha-CARBOLINE DERIVATIVES, THE PREPARATION THEREOF AND COMPOSITIONS CONTAINING THE SAME |
Country Status (8)
| Country | Link |
|---|---|
| AT (2) | AT310155B (en) |
| BE (1) | BE729855A (en) |
| CH (2) | CH553200A (en) |
| DE (1) | DE1913119A1 (en) |
| FR (1) | FR2003999A1 (en) |
| GB (1) | GB1268772A (en) |
| IE (1) | IE32705B1 (en) |
| NL (1) | NL6903973A (en) |
Cited By (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4000286A (en) | 1975-05-28 | 1976-12-28 | Merck & Co., Inc. | 3-Phenyl,3H 1,2,3 triazolo[4,5-b]pyridines |
| EP0099614A3 (en) * | 1982-07-02 | 1985-05-29 | A.H. Robins Company, Incorporated | Nitro, amino and aroylamino-n-phenylpyridinamines and their use in a process for preparing pyrido(1,4)benzodiazapines |
| WO1993020078A1 (en) * | 1992-04-03 | 1993-10-14 | The Upjohn Company | Pharmaceutically active bicyclic-heterocyclic amines |
| US5502187A (en) * | 1992-04-03 | 1996-03-26 | The Upjohn Company | Pharmaceutically active bicyclic-heterocyclic amines |
| WO1997005137A1 (en) * | 1995-07-31 | 1997-02-13 | Novo Nordisk A/S | Heterocyclic compounds, their preparation and use |
| US5696148A (en) * | 1994-03-14 | 1997-12-09 | Novo Nordisk A/S | Indole compounds and their use in treating diseases of the central nervous system |
| US5783575A (en) * | 1994-03-14 | 1998-07-21 | Novo Nordisk A/S | Antagonists, their preparation and use |
| CN1067061C (en) * | 1993-04-28 | 2001-06-13 | 泽尼卡有限公司 | Herbicidal substituted 1-phenyl or 1-pyridinyl-benzotriazoles |
| USRE37525E1 (en) | 1991-05-01 | 2002-01-22 | Henry M. Jackson Foundation | Method for treating infectious respiratory diseases |
| WO2001051479A3 (en) * | 2000-01-07 | 2002-02-14 | Warner Lambert Co | Tricyclic compounds with antiviral activity |
| US7064139B2 (en) * | 2001-10-29 | 2006-06-20 | Uniroyal Chemical Company, Inc. | Method for treating retroviral infections |
| CZ299465B6 (en) * | 2001-04-27 | 2008-08-06 | Sanofi-Aventis | Combination containing pyridoindolone derivative and anticancer agent |
| EP2161271A1 (en) * | 2008-09-08 | 2010-03-10 | Università Degli Studi Di Milano - Bicocca | Alpha-carboline inhibitors of NMP-ALK, RET, and Bcr-Abl |
| US7812165B2 (en) | 2004-04-21 | 2010-10-12 | Sanofi-Aventis | 6-substituted pyridoindolone derivatives, production and therapeutic use thereof |
| US7816368B2 (en) | 2002-10-23 | 2010-10-19 | Sanofi-Aventis | Pyridoindolone derivatives substituted in the 3-position by a heterocyclic group, their preparation and their application in therapeutics |
| US8012991B2 (en) | 2002-10-23 | 2011-09-06 | Sanofi-Aventis | Pyridoindolone derivatives substituted in the 3-position by a phenyl, their preparation and their application in therapeutics |
| US8063061B2 (en) | 2005-10-20 | 2011-11-22 | Sanofi-Aventis | 6-heteroarylpyridoindolone derivatives, their preparation and therapeutic use thereof |
| WO2015110263A1 (en) * | 2014-01-21 | 2015-07-30 | Ac Immune Sa | Carbazole and carboline compounds for use in the diagnosis, treatment, alleviation or prevention of disorders associated with amyloid or amyolid-like proteins |
| US10501457B2 (en) | 2013-03-14 | 2019-12-10 | Osteoqc Inc. | Compounds for bone growth |
| US10947236B2 (en) | 2018-08-14 | 2021-03-16 | Osteoqc Inc. | Pyrrolo-dipyridine compounds |
| US11903949B2 (en) | 2018-08-14 | 2024-02-20 | Ossifi Therapeutics Llc | Fluoro beta-carboline compounds |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE7605398L (en) * | 1975-05-28 | 1976-11-29 | Merck & Co Inc | 3H-1,2,3-TRIZOLE (4,5-B) PYRIDINES |
| JPS5536401A (en) * | 1978-06-09 | 1980-03-14 | Japan Tobacco Inc | Amino-alpha-carboline compound and mutagenic agent containing the same |
| FR2428642A1 (en) * | 1978-06-15 | 1980-01-11 | Sumitomo Chemical Co | INDOLO-ISOQUINOLEIN DERIVATIVES |
| FR3109534B1 (en) | 2020-04-22 | 2022-03-25 | Soprema | Installation and process for processing composite products based on thermoplastic materials |
-
1968
- 1968-03-15 GB GB1273168A patent/GB1268772A/en not_active Expired
-
1969
- 1969-03-14 NL NL6903973A patent/NL6903973A/xx unknown
- 1969-03-14 DE DE19691913119 patent/DE1913119A1/en active Pending
- 1969-03-14 IE IE33869A patent/IE32705B1/en unknown
- 1969-03-14 CH CH389969A patent/CH553200A/en not_active IP Right Cessation
- 1969-03-14 FR FR6907280A patent/FR2003999A1/fr not_active Withdrawn
- 1969-03-14 CH CH1271771A patent/CH561206A5/xx not_active IP Right Cessation
- 1969-03-14 AT AT736471A patent/AT310155B/en not_active IP Right Cessation
- 1969-03-14 AT AT253169A patent/AT304533B/en not_active IP Right Cessation
- 1969-03-14 BE BE729855D patent/BE729855A/xx unknown
Cited By (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4000286A (en) | 1975-05-28 | 1976-12-28 | Merck & Co., Inc. | 3-Phenyl,3H 1,2,3 triazolo[4,5-b]pyridines |
| EP0099614A3 (en) * | 1982-07-02 | 1985-05-29 | A.H. Robins Company, Incorporated | Nitro, amino and aroylamino-n-phenylpyridinamines and their use in a process for preparing pyrido(1,4)benzodiazapines |
| USRE37525E1 (en) | 1991-05-01 | 2002-01-22 | Henry M. Jackson Foundation | Method for treating infectious respiratory diseases |
| USRE38071E1 (en) | 1991-05-01 | 2003-04-08 | The Henry M. Jackson Foundation For The Advancement Of Military Medicine | Method for treating infectious respiratory diseases |
| AU675932B2 (en) * | 1992-04-03 | 1997-02-27 | Pharmacia & Upjohn Company | Pharmaceutically active bicyclic-heterocyclic amines |
| US5502187A (en) * | 1992-04-03 | 1996-03-26 | The Upjohn Company | Pharmaceutically active bicyclic-heterocyclic amines |
| WO1993020078A1 (en) * | 1992-04-03 | 1993-10-14 | The Upjohn Company | Pharmaceutically active bicyclic-heterocyclic amines |
| CN1067061C (en) * | 1993-04-28 | 2001-06-13 | 泽尼卡有限公司 | Herbicidal substituted 1-phenyl or 1-pyridinyl-benzotriazoles |
| US5696148A (en) * | 1994-03-14 | 1997-12-09 | Novo Nordisk A/S | Indole compounds and their use in treating diseases of the central nervous system |
| US5783575A (en) * | 1994-03-14 | 1998-07-21 | Novo Nordisk A/S | Antagonists, their preparation and use |
| US5945417A (en) * | 1995-07-31 | 1999-08-31 | Novo Nordisk | Heterocyclic compounds, their preparation and use |
| WO1997005137A1 (en) * | 1995-07-31 | 1997-02-13 | Novo Nordisk A/S | Heterocyclic compounds, their preparation and use |
| WO2001051479A3 (en) * | 2000-01-07 | 2002-02-14 | Warner Lambert Co | Tricyclic compounds with antiviral activity |
| US6800656B2 (en) | 2000-01-07 | 2004-10-05 | Warner Lambert Company | Tricyclic compounds and method of treating herpes virus |
| CZ299465B6 (en) * | 2001-04-27 | 2008-08-06 | Sanofi-Aventis | Combination containing pyridoindolone derivative and anticancer agent |
| US7064139B2 (en) * | 2001-10-29 | 2006-06-20 | Uniroyal Chemical Company, Inc. | Method for treating retroviral infections |
| US7816368B2 (en) | 2002-10-23 | 2010-10-19 | Sanofi-Aventis | Pyridoindolone derivatives substituted in the 3-position by a heterocyclic group, their preparation and their application in therapeutics |
| US8012991B2 (en) | 2002-10-23 | 2011-09-06 | Sanofi-Aventis | Pyridoindolone derivatives substituted in the 3-position by a phenyl, their preparation and their application in therapeutics |
| US7812165B2 (en) | 2004-04-21 | 2010-10-12 | Sanofi-Aventis | 6-substituted pyridoindolone derivatives, production and therapeutic use thereof |
| US8063061B2 (en) | 2005-10-20 | 2011-11-22 | Sanofi-Aventis | 6-heteroarylpyridoindolone derivatives, their preparation and therapeutic use thereof |
| EP2161271A1 (en) * | 2008-09-08 | 2010-03-10 | Università Degli Studi Di Milano - Bicocca | Alpha-carboline inhibitors of NMP-ALK, RET, and Bcr-Abl |
| JP2012501984A (en) * | 2008-09-08 | 2012-01-26 | ウニヴェルシダ’デリ ストゥディ ディ ミラノ−ビコッカ | Α-carboline inhibitors of NPM-ALK, RET and BCR-ABL |
| US8895744B2 (en) | 2008-09-08 | 2014-11-25 | Universita' Degli Studi Di Milano-Bicocca | Alfa-carboline inhibitors of NPM-ALK, RET, and Bcr-Abl |
| US10501457B2 (en) | 2013-03-14 | 2019-12-10 | Osteoqc Inc. | Compounds for bone growth |
| US11267814B2 (en) | 2013-03-14 | 2022-03-08 | OsteoQC, Inc. | Compounds for bone growth |
| WO2015110263A1 (en) * | 2014-01-21 | 2015-07-30 | Ac Immune Sa | Carbazole and carboline compounds for use in the diagnosis, treatment, alleviation or prevention of disorders associated with amyloid or amyolid-like proteins |
| US10662193B2 (en) | 2014-01-21 | 2020-05-26 | Ac Immune Sa | Carbazole and carboline compounds for use in the diagnosis, treatment, alleviation or prevention of disorders associated with amyloid or amyloid-like proteins |
| US10947236B2 (en) | 2018-08-14 | 2021-03-16 | Osteoqc Inc. | Pyrrolo-dipyridine compounds |
| US11655250B2 (en) | 2018-08-14 | 2023-05-23 | Osteoqc Inc. | Pyrrolo-dipyridine compounds |
| US11903949B2 (en) | 2018-08-14 | 2024-02-20 | Ossifi Therapeutics Llc | Fluoro beta-carboline compounds |
| US12195461B2 (en) | 2018-08-14 | 2025-01-14 | Ossifi Therapeutics Llc | Pyrrolo-dipyridine compounds |
| US12324809B2 (en) | 2018-08-14 | 2025-06-10 | Ossifi Therapeutics Llc | Fluoro beta-carboline compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| AT304533B (en) | 1973-01-10 |
| IE32705L (en) | 1969-09-15 |
| IE32705B1 (en) | 1973-10-31 |
| NL6903973A (en) | 1969-09-17 |
| BE729855A (en) | 1969-09-15 |
| AT310155B (en) | 1973-09-25 |
| FR2003999A1 (en) | 1969-11-14 |
| DE1913119A1 (en) | 1970-08-06 |
| CH553200A (en) | 1974-08-30 |
| CH561206A5 (en) | 1975-04-30 |
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