GB1395110A - Derivatives of pyridine-3-acetic acid - Google Patents
Derivatives of pyridine-3-acetic acidInfo
- Publication number
- GB1395110A GB1395110A GB4300073A GB4300073A GB1395110A GB 1395110 A GB1395110 A GB 1395110A GB 4300073 A GB4300073 A GB 4300073A GB 4300073 A GB4300073 A GB 4300073A GB 1395110 A GB1395110 A GB 1395110A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compounds
- formula
- derivatives
- acetic acid
- sept
- 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
- WGNUNYPERJMVRM-UHFFFAOYSA-N 3-pyridylacetic acid Chemical class OC(=O)CC1=CC=CN=C1 WGNUNYPERJMVRM-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 5
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 abstract 2
- 230000003301 hydrolyzing effect Effects 0.000 abstract 2
- OUTYHBMCWGHPCD-UHFFFAOYSA-N 2-(2-methyl-6-phenylpyridin-3-yl)acetic acid Chemical class C1=C(CC(O)=O)C(C)=NC(C=2C=CC=CC=2)=C1 OUTYHBMCWGHPCD-UHFFFAOYSA-N 0.000 abstract 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical class CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 1
- 150000001204 N-oxides Chemical class 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 230000000202 analgesic effect Effects 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 150000003841 chloride salts Chemical class 0.000 abstract 1
- 238000009792 diffusion process Methods 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
- -1 wherein R 1 is H 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
- C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/757—Unsaturated compounds containing a keto groups being part of a ring containing —CHO groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/86—Ketones containing a keto group bound to a six-membered aromatic ring containing —CHO groups
-
- 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
- C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/55—Acids; Esters
-
- 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/10—Aza-phenanthrenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
Abstract
1395110 Derivatives of 2-methyl-6-phenylpyridine-3-acetic acid SERDEX-SOC D'- ETUDES DE RECHERCHES DE DIFFUSION ET D'EXPLOITATION 13 Sept 1973 [13 Sept 1972] 43000/73 Heading C2C The invention comprises compounds of formula and their esters, N-oxides and pharmacologically acceptable salts, wherein R 1 is H, halogen or C 1-6 alkyl or alkoxy; R 2 is H or Me; and either A is H and B is Ph (possibly R 1 -substituted), or A-B is -CH 2 CH 2 - or -OCH 2 -. These compounds may be prepared by (a) utilizing analogues of the above compounds but in which -CHR 2 -CO 2 H is replaced by CO 2 Et or COMe, reducing to the corresponding alcohols which are converted to the chlorides and thus to the nitriles, and hydrolyzing the latter; or (b) reacting the initial methylketones with S+ morpholine and hydrolysing the thiomorpholides of the above compounds so formed. Starting materials prepared have the formula R 1 (A)C 6 H 3 COCHBCHO and (apparently) where R 1 , A and B have the same meanings as above. Therapeutic compositions having antiinflammatory and analgesic activity comprise compounds of the above formula and are preferably administered orally.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR7232383A FR2198737B1 (en) | 1972-09-13 | 1972-09-13 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1395110A true GB1395110A (en) | 1975-05-21 |
Family
ID=9104203
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB4300073A Expired GB1395110A (en) | 1972-09-13 | 1973-09-13 | Derivatives of pyridine-3-acetic acid |
Country Status (6)
Country | Link |
---|---|
BE (1) | BE804802A (en) |
CH (1) | CH580076A5 (en) |
DE (1) | DE2345924A1 (en) |
ES (1) | ES418841A1 (en) |
FR (1) | FR2198737B1 (en) |
GB (1) | GB1395110A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7271266B2 (en) * | 2002-03-28 | 2007-09-18 | Merck & Co., Inc. | Substituted 2,3-diphenyl pyridines |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2856684B1 (en) * | 2003-06-26 | 2008-04-11 | Sanofi Synthelabo | DIPHENYLPYRIDINE DERIVATIVES, THEIR PREPARATION AND THEIR THERAPEUTIC APPLICATION |
FR2876691B1 (en) * | 2004-10-18 | 2006-12-29 | Sanofi Aventis Sa | PYRIDINE DERIVATIVES, THEIR PREPARATION, THEIR THERAPEUTIC APPLICATION |
CN109575041B (en) * | 2018-07-30 | 2021-04-16 | 郑州大学 | Polycyclic pyridine compound and preparation method thereof |
-
1972
- 1972-09-13 FR FR7232383A patent/FR2198737B1/fr not_active Expired
-
1973
- 1973-09-11 CH CH1302173A patent/CH580076A5/xx not_active IP Right Cessation
- 1973-09-12 DE DE19732345924 patent/DE2345924A1/en active Pending
- 1973-09-12 ES ES418841A patent/ES418841A1/en not_active Expired
- 1973-09-13 BE BE135602A patent/BE804802A/en unknown
- 1973-09-13 GB GB4300073A patent/GB1395110A/en not_active Expired
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7271266B2 (en) * | 2002-03-28 | 2007-09-18 | Merck & Co., Inc. | Substituted 2,3-diphenyl pyridines |
AU2003225964B2 (en) * | 2002-03-28 | 2008-11-20 | Merck Sharp & Dohme Corp. | Substituted 2,3-diphenyl pyridines |
Also Published As
Publication number | Publication date |
---|---|
FR2198737A1 (en) | 1974-04-05 |
FR2198737B1 (en) | 1975-11-28 |
CH580076A5 (en) | 1976-09-30 |
ES418841A1 (en) | 1976-03-16 |
DE2345924A1 (en) | 1974-03-21 |
BE804802A (en) | 1974-01-02 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PS | Patent sealed | ||
PCNP | Patent ceased through non-payment of renewal fee |