CN1129906A - N-烷基化的1，4-二氢吡啶二羧酸酯作为药物的应用 - Google Patents
N-烷基化的1，4-二氢吡啶二羧酸酯作为药物的应用 Download PDFInfo
- Publication number
- CN1129906A CN1129906A CN94193170A CN94193170A CN1129906A CN 1129906 A CN1129906 A CN 1129906A CN 94193170 A CN94193170 A CN 94193170A CN 94193170 A CN94193170 A CN 94193170A CN 1129906 A CN1129906 A CN 1129906A
- Authority
- CN
- China
- Prior art keywords
- general formula
- chemical compound
- described general
- application
- medicine
- 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
- 239000003814 drug Substances 0.000 title claims abstract description 11
- SYHPGXUWPYJXOO-UHFFFAOYSA-N 1,4-dihydropyridine-2,3-dicarboxylic acid Chemical class OC(=O)C1=C(C(O)=O)NC=CC1 SYHPGXUWPYJXOO-UHFFFAOYSA-N 0.000 title abstract description 3
- 208000037803 restenosis Diseases 0.000 claims abstract description 7
- 230000000879 anti-atherosclerotic effect Effects 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 19
- 230000002792 vascular Effects 0.000 claims description 10
- 201000001320 Atherosclerosis Diseases 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- -1 nitro, hydroxyl Chemical group 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical compound C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 230000002152 alkylating effect Effects 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 210000000329 smooth muscle myocyte Anatomy 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000005605 benzo group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- 239000012752 auxiliary agent Substances 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 230000008069 intimal proliferation Effects 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 238000002399 angioplasty Methods 0.000 abstract description 6
- 210000004204 blood vessel Anatomy 0.000 abstract description 5
- 229940079593 drug Drugs 0.000 abstract description 2
- 238000001356 surgical procedure Methods 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 208000035126 Facies Diseases 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 150000003222 pyridines Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical class COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 2
- 208000034827 Neointima Diseases 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 150000003935 benzaldehydes Chemical class 0.000 description 2
- 230000004663 cell proliferation Effects 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- 239000003643 water by type Substances 0.000 description 2
- ZYMCBJWUWHHVRX-UHFFFAOYSA-N (4-nitrophenyl)-phenylmethanone Chemical compound C1=CC([N+](=O)[O-])=CC=C1C(=O)C1=CC=CC=C1 ZYMCBJWUWHHVRX-UHFFFAOYSA-N 0.000 description 1
- HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 206010047139 Vasoconstriction Diseases 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
- 230000001028 anti-proliverative effect Effects 0.000 description 1
- 210000000709 aorta Anatomy 0.000 description 1
- 230000000680 avirulence Effects 0.000 description 1
- 238000009395 breeding Methods 0.000 description 1
- 230000001488 breeding effect Effects 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000013171 endarterectomy Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical class [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical class [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 230000025033 vasoconstriction Effects 0.000 description 1
Classifications
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/455—Nicotinic acids, e.g. niacin; Derivatives thereof, e.g. esters, amides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Heart & Thoracic Surgery (AREA)
- Vascular Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Cardiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Urology & Nephrology (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4328884A DE4328884A1 (de) | 1993-08-27 | 1993-08-27 | Verwendung von N-alkylierten 1,4-Dihydropyridincarbonsäureestern als Arzneimittel |
| DEP4328884.7 | 1993-08-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1129906A true CN1129906A (zh) | 1996-08-28 |
Family
ID=6496196
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN94193170A Pending CN1129906A (zh) | 1993-08-27 | 1994-08-16 | N-烷基化的1，4-二氢吡啶二羧酸酯作为药物的应用 |
Country Status (13)
| Country | Link |
|---|---|
| EP (1) | EP0714301A1 (no) |
| JP (1) | JPH09501923A (no) |
| KR (1) | KR960703594A (no) |
| CN (1) | CN1129906A (no) |
| AU (1) | AU7613594A (no) |
| BG (1) | BG100367A (no) |
| CA (1) | CA2170285A1 (no) |
| CZ (1) | CZ43896A3 (no) |
| DE (1) | DE4328884A1 (no) |
| HU (1) | HUT75302A (no) |
| NO (1) | NO960777L (no) |
| PL (1) | PL313116A1 (no) |
| WO (1) | WO1995005823A1 (no) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19741694C2 (de) * | 1997-09-18 | 2002-10-31 | Schering Ag | Verwendung von Komplexen, deren Ligand ein Bis-Amin-Oxim-Derivat oder ein N¶2¶S¶2¶-Derivat und deren Zentralatom ein Radionuklid ist |
| DE60214428T2 (de) * | 2001-12-20 | 2007-09-20 | Bayer Healthcare Ag | 1, 4-dihydro-1, 4-diphenylpyridin-derivate |
| US10258498B2 (en) * | 2011-11-24 | 2019-04-16 | Richter Gedeon Nyrt. | 1,4-dihydropyridine derivatives with Hsp modulating activity |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3222367A1 (de) * | 1982-06-15 | 1983-12-15 | Bayer Ag, 5090 Leverkusen | Verwendung von 1,4-dihydropyridinen in antiarteriosklerotika und deren herstellung |
| EP0169009A3 (en) * | 1984-07-17 | 1988-08-31 | FISONS plc | Novel dihydropyridine derivatives and their production, formulation and use as pharmaceuticals |
| DE4011695A1 (de) * | 1990-04-11 | 1991-10-17 | Bayer Ag | Verwendung von n-alkylierten 1,4-dihydropyridindicarbonsaeureestern als arzneimittel, neue verbindungen und verfahren zu ihrer herstellung |
-
1993
- 1993-08-27 DE DE4328884A patent/DE4328884A1/de not_active Withdrawn
-
1994
- 1994-08-16 EP EP94926199A patent/EP0714301A1/de not_active Withdrawn
- 1994-08-16 WO PCT/EP1994/002723 patent/WO1995005823A1/de not_active Application Discontinuation
- 1994-08-16 JP JP7507325A patent/JPH09501923A/ja not_active Ceased
- 1994-08-16 CA CA002170285A patent/CA2170285A1/en not_active Abandoned
- 1994-08-16 KR KR1019960700944A patent/KR960703594A/ko not_active Application Discontinuation
- 1994-08-16 CZ CZ96438A patent/CZ43896A3/cs unknown
- 1994-08-16 HU HU9600472A patent/HUT75302A/hu unknown
- 1994-08-16 CN CN94193170A patent/CN1129906A/zh active Pending
- 1994-08-16 PL PL94313116A patent/PL313116A1/xx unknown
- 1994-08-16 AU AU76135/94A patent/AU7613594A/en not_active Abandoned
-
1996
- 1996-02-19 BG BG100367A patent/BG100367A/xx unknown
- 1996-02-26 NO NO960777A patent/NO960777L/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BG100367A (en) | 1996-07-31 |
| HUT75302A (en) | 1997-05-28 |
| PL313116A1 (en) | 1996-06-10 |
| KR960703594A (ko) | 1996-08-31 |
| HU9600472D0 (en) | 1996-04-29 |
| NO960777L (no) | 1996-04-10 |
| JPH09501923A (ja) | 1997-02-25 |
| EP0714301A1 (de) | 1996-06-05 |
| DE4328884A1 (de) | 1995-03-02 |
| NO960777D0 (no) | 1996-02-26 |
| AU7613594A (en) | 1995-03-21 |
| WO1995005823A1 (de) | 1995-03-02 |
| CZ43896A3 (en) | 1996-05-15 |
| CA2170285A1 (en) | 1995-03-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C01 | Deemed withdrawal of patent application (patent law 1993) | ||
| WD01 | Invention patent application deemed withdrawn after publication |