GB1495153A - Prostanoic acid derivatives - Google Patents
Prostanoic acid derivativesInfo
- Publication number
- GB1495153A GB1495153A GB5024974A GB5024974A GB1495153A GB 1495153 A GB1495153 A GB 1495153A GB 5024974 A GB5024974 A GB 5024974A GB 5024974 A GB5024974 A GB 5024974A GB 1495153 A GB1495153 A GB 1495153A
- Authority
- GB
- United Kingdom
- Prior art keywords
- chlorophenoxy
- difluoro
- oxo
- methyl
- trans
- 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
- WGJJROVFWIXTPA-OALUTQOASA-N prostanoic acid Chemical class CCCCCCCC[C@H]1CCC[C@@H]1CCCCCCC(O)=O WGJJROVFWIXTPA-OALUTQOASA-N 0.000 title 1
- -1 carboxy, hydroxymethyl Chemical group 0.000 abstract 9
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 125000003545 alkoxy group Chemical group 0.000 abstract 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 2
- 239000005977 Ethylene Substances 0.000 abstract 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 abstract 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 2
- 125000004043 oxo group Chemical group O=* 0.000 abstract 2
- 229940094443 oxytocics prostaglandins Drugs 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 150000003180 prostaglandins Chemical class 0.000 abstract 2
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 abstract 1
- HGEZLXPHRVDLKS-UHFFFAOYSA-N 1-(3-chlorophenoxy)-3-dimethoxyphosphoryl-1,1-difluoropropan-2-one Chemical compound ClC=1C=C(OC(C(CP(OC)(OC)=O)=O)(F)F)C=CC1 HGEZLXPHRVDLKS-UHFFFAOYSA-N 0.000 abstract 1
- HUHXLHLWASNVDB-UHFFFAOYSA-N 2-(oxan-2-yloxy)oxane Chemical compound O1CCCCC1OC1OCCCC1 HUHXLHLWASNVDB-UHFFFAOYSA-N 0.000 abstract 1
- SWHRMXRRKOZOGS-UHFFFAOYSA-N 3-dimethoxyphosphoryl-1,1-difluoro-1-(3-methylphenoxy)propan-2-one Chemical compound FC(C(CP(OC)(OC)=O)=O)(OC=1C=C(C=CC1)C)F SWHRMXRRKOZOGS-UHFFFAOYSA-N 0.000 abstract 1
- 125000004442 acylamino group Chemical group 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000003302 alkenyloxy group Chemical group 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- VONWDASPFIQPDY-UHFFFAOYSA-N dimethyl methylphosphonate Chemical compound COP(C)(=O)OC VONWDASPFIQPDY-UHFFFAOYSA-N 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- TYLHFUCWUZBTQJ-UHFFFAOYSA-N methyl 2,2-difluoro-2-(3-methylphenoxy)acetate Chemical compound FC(C(=O)OC)(OC=1C=C(C=CC1)C)F TYLHFUCWUZBTQJ-UHFFFAOYSA-N 0.000 abstract 1
- BQDUEPCGCDLJGS-UHFFFAOYSA-N methyl 2-(3-chlorophenoxy)-2,2-difluoroacetate Chemical compound COC(C(F)(F)OC1=CC(=CC=C1)Cl)=O BQDUEPCGCDLJGS-UHFFFAOYSA-N 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 238000010561 standard procedure Methods 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no 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
- C07D309/10—Oxygen atoms
- C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
1495153 Prostaglandins IMPERIAL CHEMICAL INDUSTRIES Ltd 17 Oct 1975 [20 Nov 1974] 50249/74 Headings C2C and C2P [Also in Division A5] The invention comprises prostaglandins of the Formula I wherein either R<SP>1</SP> is carboxy, hydroxymethyl or (C 1-10 alkoxy)carbonyl, R<SP>2</SP> is OH or C 1-4 alkanoyloxy and R<SP>3</SP> is H, or R<SP>1</SP> is carboxy or (C 1-10 alkoxy)carbonyl and R<SP>2</SP> and R<SP>3</SP> together form an oxo group; A<SP>1</SP> is ethylene or cis- or transvinylene, R<SP>2</SP> is ethylene or trans-vinylene; R<SP>4</SP>, R<SP>7</SP> and R<SP>8</SP> are H or C 1-4 alkyl, R<SP>5</SP> is H, F or C 1-4 alkyl and R<SP>6</SP> is phenyl, naphthyl or tetrahydronaphthyl, optionally substituted by one or more halogen atoms, OH, NO 2 , phenyl, C 1-4 alkyl, C 2-4 alkenyl, C 1-4 haloalkyl, C 1-4 alkoxy, C 2-4 alkenyloxy, C 1-4 acylamino or di-(C 1-4 alkyl) amino radicals and for those compounds wherein R<SP>1</SP> is carboxy the pharmaceutically and veterinarily acceptable salts thereof and their preparation by standard methods. The following intermediates are also prepared: methyl - (3 - chlorophenoxy) - difluoroacetate; methyl - (3 - tolyloxy)difluoroacetate; 4#-[4- (3 - chlorophenoxy) - 4,4 - difluoro - 3 - oxo (and hydroxy) - but - 1 - trans - enyl] - 3,3a#,4,5,6,6c#- hexahydro - 5α - (4 - phenylbenzoyloxy) - 2H- cyclopenta[b]furan-2-one; 4#-[4-(3-chlorophenoxy) - 4,4 - difluoro - 3 - hydroxybut - 1 - transenyl] - 3,3a#,4,5,6,6a# - hexahydro - 5α - hydroxy - 2H - cyclopenta[b]furan - 2- one and its (bis(tetrahydropyranyl) ether; 4#-[4-(3- chlorophenoxy) - 4,4 - difluoro - 3 - (2 - tetrahydropyranyloxy) - 1 - trans - butenyl] - 3,3a#- 4,5,6,6a# - hexahydro - 5α - (2 - tetrahydropyranyloxy) - 2H - cyclopenta[b]furan - 2 - ol; 16 - (3 - chlorophenoxy) - 16,16 - difluoro - 9α- hydroxy (or 9-oxo)-11α,15-bis(2-tetrahydropyranyloxy) - 17,18,19,20 - tetranor - 5 - cis,13- trans-prostadienoic acid; and methyl-16,16- difluoro - 15 - hydroxy (or oxo) - 9α,11α - di(4- phenylbenzoyloxy) - 16 - (3 - tolyloxy) - 17,18- 19,20 - tetranor - 5 - cis,13 - trans - prostadienoate. Dimethyl 3-(3-chlorophenoxy)-3,3-difluoro-2- oxo-propylphosphonate and dimethyl 3,3-difluoro- 2 - oxo - 3 - (3 - tolyloxy)propylphosphonate are prepared by reacting dimethyl methyl phosphonate with methyl (3-chlorophenoxy) difluoroacetate and methyl (3-tolyloxy)diflurooacetate respectively in the presence of butyllithium.
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5024974A GB1495153A (en) | 1974-11-20 | 1974-11-20 | Prostanoic acid derivatives |
| AU86100/75A AU8610075A (en) | 1974-11-20 | 1975-10-29 | Prostanoic acid derivative |
| FR7535389A FR2291742A1 (en) | 1974-11-20 | 1975-11-19 | NEW PROSTANOIC ACID DERIVATIVES, THEIR PREPARATION PROCESS AND MEDICINAL PRODUCTS CONTAINING THEM |
| JP13970675A JPS5180843A (en) | 1974-11-20 | 1975-11-20 | PUROSUTANOITSUKUSAN JUDOTAINO SEIHO |
| DE19752552109 DE2552109A1 (en) | 1974-11-20 | 1975-11-20 | PROSTANIC ACID DERIVATIVES |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5024974A GB1495153A (en) | 1974-11-20 | 1974-11-20 | Prostanoic acid derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1495153A true GB1495153A (en) | 1977-12-14 |
Family
ID=10455225
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5024974A Expired GB1495153A (en) | 1974-11-20 | 1974-11-20 | Prostanoic acid derivatives |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS5180843A (en) |
| AU (1) | AU8610075A (en) |
| DE (1) | DE2552109A1 (en) |
| FR (1) | FR2291742A1 (en) |
| GB (1) | GB1495153A (en) |
-
1974
- 1974-11-20 GB GB5024974A patent/GB1495153A/en not_active Expired
-
1975
- 1975-10-29 AU AU86100/75A patent/AU8610075A/en not_active Expired
- 1975-11-19 FR FR7535389A patent/FR2291742A1/en active Granted
- 1975-11-20 DE DE19752552109 patent/DE2552109A1/en not_active Withdrawn
- 1975-11-20 JP JP13970675A patent/JPS5180843A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DE2552109A1 (en) | 1976-05-26 |
| JPS5180843A (en) | 1976-07-15 |
| AU8610075A (en) | 1977-05-05 |
| FR2291742A1 (en) | 1976-06-18 |
| FR2291742B1 (en) | 1979-06-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |