GB1387306A - Derivatives of pyrazole-5 acetic acid process for their preparation and their use in therapy - Google Patents
Derivatives of pyrazole-5 acetic acid process for their preparation and their use in therapyInfo
- Publication number
- GB1387306A GB1387306A GB1218272A GB1218272A GB1387306A GB 1387306 A GB1387306 A GB 1387306A GB 1218272 A GB1218272 A GB 1218272A GB 1218272 A GB1218272 A GB 1218272A GB 1387306 A GB1387306 A GB 1387306A
- Authority
- GB
- United Kingdom
- Prior art keywords
- benzyl
- alkyl
- ethyl
- reacted
- prepared
- 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 title abstract 7
- 238000000034 method Methods 0.000 title abstract 2
- 238000002560 therapeutic procedure Methods 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 abstract 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 4
- -1 pyrrolidino, piperidino Chemical group 0.000 abstract 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 229940009098 aspartate Drugs 0.000 abstract 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N methyl cyanide Natural products CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- YEFGPLDLJYMUOG-UHFFFAOYSA-N (2-benzyl-4,5-diphenylpyrazol-3-yl)methanol Chemical compound OCC1=C(C=2C=CC=CC=2)C(C=2C=CC=CC=2)=NN1CC1=CC=CC=C1 YEFGPLDLJYMUOG-UHFFFAOYSA-N 0.000 abstract 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- QNHXTQNNJSORRV-UHFFFAOYSA-N 1-benzyl-5-(chloromethyl)-3,4-diphenylpyrazole Chemical compound ClCC1=C(C=2C=CC=CC=2)C(C=2C=CC=CC=2)=NN1CC1=CC=CC=C1 QNHXTQNNJSORRV-UHFFFAOYSA-N 0.000 abstract 1
- JKISWSOCTWDLSE-UHFFFAOYSA-N 2-(2,4,5-triphenylpyrazol-3-yl)acetonitrile Chemical compound N#CCC1=C(C=2C=CC=CC=2)C(C=2C=CC=CC=2)=NN1C1=CC=CC=C1 JKISWSOCTWDLSE-UHFFFAOYSA-N 0.000 abstract 1
- PPIZJRSRMTZRPE-UHFFFAOYSA-N 2-(2-benzyl-4,5-diphenylpyrazol-3-yl)acetonitrile Chemical compound N#CCC1=C(C=2C=CC=CC=2)C(C=2C=CC=CC=2)=NN1CC1=CC=CC=C1 PPIZJRSRMTZRPE-UHFFFAOYSA-N 0.000 abstract 1
- QTGOVFBOVSNHKB-UHFFFAOYSA-N 2-[2-(2-methylpropyl)-4,5-diphenylpyrazol-3-yl]acetonitrile Chemical compound N#CCC=1N(CC(C)C)N=C(C=2C=CC=CC=2)C=1C1=CC=CC=C1 QTGOVFBOVSNHKB-UHFFFAOYSA-N 0.000 abstract 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 230000001754 anti-pyretic effect Effects 0.000 abstract 1
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical compound C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 abstract 1
- JRXXLCKWQFKACW-UHFFFAOYSA-N biphenylacetylene Chemical group C1=CC=CC=C1C#CC1=CC=CC=C1 JRXXLCKWQFKACW-UHFFFAOYSA-N 0.000 abstract 1
- 150000007942 carboxylates Chemical class 0.000 abstract 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 abstract 1
- NVRSPIKUPKOSIY-UHFFFAOYSA-N chembl1743348 Chemical compound CC=1N=NOC=1O NVRSPIKUPKOSIY-UHFFFAOYSA-N 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 230000000911 decarboxylating effect Effects 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- ULOLIZHBYWAICY-UHFFFAOYSA-N ethyl 2-(benzylamino)acetate Chemical compound CCOC(=O)CNCC1=CC=CC=C1 ULOLIZHBYWAICY-UHFFFAOYSA-N 0.000 abstract 1
- CBMUUNRLWHVFMU-UHFFFAOYSA-N ethyl 2-[amino(benzyl)amino]acetate Chemical compound CCOC(=O)CN(N)CC1=CC=CC=C1 CBMUUNRLWHVFMU-UHFFFAOYSA-N 0.000 abstract 1
- ARXORJDWJJPBMM-UHFFFAOYSA-N ethyl 2-[benzyl(nitroso)amino]acetate Chemical compound CCOC(=O)CN(N=O)CC1=CC=CC=C1 ARXORJDWJJPBMM-UHFFFAOYSA-N 0.000 abstract 1
- UJYMAYNIRQVOCK-UHFFFAOYSA-N ethyl 2-benzyl-4,5-diphenylpyrazole-3-carboxylate Chemical compound CCOC(=O)C1=C(C=2C=CC=CC=2)C(C=2C=CC=CC=2)=NN1CC1=CC=CC=C1 UJYMAYNIRQVOCK-UHFFFAOYSA-N 0.000 abstract 1
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 abstract 1
- NKHAVTQWNUWKEO-UHFFFAOYSA-N fumaric acid monomethyl ester Natural products COC(=O)C=CC(O)=O NKHAVTQWNUWKEO-UHFFFAOYSA-N 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 abstract 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical class OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 abstract 1
- NKHAVTQWNUWKEO-IHWYPQMZSA-N methyl hydrogen fumarate Chemical compound COC(=O)\C=C/C(O)=O NKHAVTQWNUWKEO-IHWYPQMZSA-N 0.000 abstract 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000000546 pharmaceutical excipient Substances 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 abstract 1
- 235000010288 sodium nitrite Nutrition 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- 125000001391 thioamide group Chemical group 0.000 abstract 1
- 239000011701 zinc Substances 0.000 abstract 1
- 229910052725 zinc Inorganic materials 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/04—Formation of amino groups in compounds containing carboxyl groups
- C07C227/06—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid
- C07C227/08—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid by reaction of ammonia or amines with acids containing functional groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/04—1,2,3-Oxadiazoles; Hydrogenated 1,2,3-oxadiazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1218272A GB1387306A (en) | 1972-03-15 | 1972-03-15 | Derivatives of pyrazole-5 acetic acid process for their preparation and their use in therapy |
| BE128532A BE796465A (fr) | 1972-03-15 | 1973-03-08 | Nouveaux derives de l'acide pyrazole-5-acetique leur procede de preparation et leurs applications en therapeutique |
| CH347973A CH581117A5 (enrdf_load_stackoverflow) | 1972-03-15 | 1973-03-10 | |
| DE19732312256 DE2312256C3 (de) | 1972-03-15 | 1973-03-12 | 5-Pyrazol-essigsäurederivate, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Mittel |
| SE7303570A SE400556B (sv) | 1972-03-15 | 1973-03-14 | Forfarande for famstellning av nya 5-ettiksyra-pyrasolderivat |
| FR7309035A FR2176018B1 (enrdf_load_stackoverflow) | 1972-03-15 | 1973-03-14 | |
| CA166,328A CA1011745A (fr) | 1972-03-15 | 1973-03-14 | Derives de l'acide pyrazole-5-acetique, leur procede de preparation et leurs applications en therapeutiques |
| AT226873A AT326649B (de) | 1972-03-15 | 1973-03-14 | Verfahren zur herstellung neuer 5-pyrazolessigsäurederivate |
| ZA731818A ZA731818B (en) | 1972-03-15 | 1973-03-15 | Derivatives of pyrazole-5-acetic acid and methods of preparing same |
| NLAANVRAGE7303658,A NL181273C (nl) | 1972-03-15 | 1973-03-15 | Werkwijze voor het bereiden of vervaardigen van een geneesmiddel met ontstekingswerende, analgetische en antipyretische werking en werkwijze voor het bereiden van difenylpyrazolylazijnzuurverbindingen. |
| JP3045973A JPS5337863B2 (enrdf_load_stackoverflow) | 1972-03-15 | 1973-03-15 | |
| US05/589,513 US3984431A (en) | 1972-03-15 | 1975-06-23 | Derivatives of pyrazole-5-acetic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1218272A GB1387306A (en) | 1972-03-15 | 1972-03-15 | Derivatives of pyrazole-5 acetic acid process for their preparation and their use in therapy |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1387306A true GB1387306A (en) | 1975-03-12 |
Family
ID=9999842
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1218272A Expired GB1387306A (en) | 1972-03-15 | 1972-03-15 | Derivatives of pyrazole-5 acetic acid process for their preparation and their use in therapy |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS5337863B2 (enrdf_load_stackoverflow) |
| AT (1) | AT326649B (enrdf_load_stackoverflow) |
| BE (1) | BE796465A (enrdf_load_stackoverflow) |
| CA (1) | CA1011745A (enrdf_load_stackoverflow) |
| CH (1) | CH581117A5 (enrdf_load_stackoverflow) |
| FR (1) | FR2176018B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1387306A (enrdf_load_stackoverflow) |
| NL (1) | NL181273C (enrdf_load_stackoverflow) |
| SE (1) | SE400556B (enrdf_load_stackoverflow) |
| ZA (1) | ZA731818B (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2320093A1 (fr) * | 1975-08-05 | 1977-03-04 | Sogeras | Nouveaux acides diphenyl-pyrazole-5-acetiques |
-
1972
- 1972-03-15 GB GB1218272A patent/GB1387306A/en not_active Expired
-
1973
- 1973-03-08 BE BE128532A patent/BE796465A/xx not_active IP Right Cessation
- 1973-03-10 CH CH347973A patent/CH581117A5/xx not_active IP Right Cessation
- 1973-03-14 FR FR7309035A patent/FR2176018B1/fr not_active Expired
- 1973-03-14 SE SE7303570A patent/SE400556B/xx unknown
- 1973-03-14 AT AT226873A patent/AT326649B/de not_active IP Right Cessation
- 1973-03-14 CA CA166,328A patent/CA1011745A/fr not_active Expired
- 1973-03-15 ZA ZA731818A patent/ZA731818B/xx unknown
- 1973-03-15 NL NLAANVRAGE7303658,A patent/NL181273C/xx not_active IP Right Cessation
- 1973-03-15 JP JP3045973A patent/JPS5337863B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH581117A5 (enrdf_load_stackoverflow) | 1976-10-29 |
| JPS5337863B2 (enrdf_load_stackoverflow) | 1978-10-12 |
| JPS4992067A (enrdf_load_stackoverflow) | 1974-09-03 |
| AT326649B (de) | 1975-12-29 |
| NL181273C (nl) | 1987-07-16 |
| FR2176018A1 (enrdf_load_stackoverflow) | 1973-10-26 |
| BE796465A (fr) | 1973-07-02 |
| ZA731818B (en) | 1974-04-24 |
| SE400556B (sv) | 1978-04-03 |
| ATA226873A (de) | 1975-03-15 |
| CA1011745A (fr) | 1977-06-07 |
| NL7303658A (enrdf_load_stackoverflow) | 1973-09-18 |
| DE2312256A1 (de) | 1973-09-27 |
| DE2312256B2 (de) | 1977-03-10 |
| NL181273B (nl) | 1987-02-16 |
| FR2176018B1 (enrdf_load_stackoverflow) | 1977-01-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |