GB1356581A - Cyclopentane derivatives - Google Patents
Cyclopentane derivativesInfo
- Publication number
- GB1356581A GB1356581A GB48131/70*2A GB4813170A GB1356581A GB 1356581 A GB1356581 A GB 1356581A GB 4813170 A GB4813170 A GB 4813170A GB 1356581 A GB1356581 A GB 1356581A
- Authority
- GB
- United Kingdom
- Prior art keywords
- tetrahydropyran
- yloxy
- trans
- reacting
- cis
- 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
- 125000001511 cyclopentyl group Chemical class [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 title 1
- -1 oxo radical Chemical class 0.000 abstract 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 6
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 abstract 6
- 239000002253 acid Substances 0.000 abstract 6
- 239000007983 Tris buffer Substances 0.000 abstract 4
- 125000004423 acyloxy group Chemical group 0.000 abstract 3
- 125000003545 alkoxy group Chemical group 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 230000003301 hydrolyzing effect Effects 0.000 abstract 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 3
- 229940094443 oxytocics prostaglandins Drugs 0.000 abstract 3
- 150000003180 prostaglandins Chemical class 0.000 abstract 3
- YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 abstract 2
- MLOSJPZSZWUDSK-UHFFFAOYSA-N 4-carboxybutyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCCC(=O)O)C1=CC=CC=C1 MLOSJPZSZWUDSK-UHFFFAOYSA-N 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 abstract 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 abstract 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 150000008064 anhydrides Chemical class 0.000 abstract 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 150000001940 cyclopentanes Chemical class 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 abstract 1
- CPEONABTMRSIKA-UHFFFAOYSA-N 1,4$l^{2}-oxazinane Chemical compound C1COCC[N]1 CPEONABTMRSIKA-UHFFFAOYSA-N 0.000 abstract 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 abstract 1
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 abstract 1
- QHINYJQPBCMLCJ-UHFFFAOYSA-N 3,3a,4,5,6,6a-hexahydro-2h-cyclopenta[b]furan Chemical compound C1COC2CCCC21 QHINYJQPBCMLCJ-UHFFFAOYSA-N 0.000 abstract 1
- CPVNCBJFUQQXSU-UHFFFAOYSA-N 5-triphenylphosphaniumylpentanoate Chemical class C1(=CC=CC=C1)[P+](CCCCC(=O)[O-])(C1=CC=CC=C1)C1=CC=CC=C1 CPVNCBJFUQQXSU-UHFFFAOYSA-N 0.000 abstract 1
- 208000009079 Bronchial Spasm Diseases 0.000 abstract 1
- 208000014181 Bronchial disease Diseases 0.000 abstract 1
- 206010006482 Bronchospasm Diseases 0.000 abstract 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 abstract 1
- 208000001953 Hypotension Diseases 0.000 abstract 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 abstract 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 abstract 1
- PQGAHNJECSVDEI-UHFFFAOYSA-N [CH2]CCCCC Chemical compound [CH2]CCCCC PQGAHNJECSVDEI-UHFFFAOYSA-N 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 150000001450 anions Chemical class 0.000 abstract 1
- RHDGNLCLDBVESU-UHFFFAOYSA-N but-3-en-4-olide Chemical compound O=C1CC=CO1 RHDGNLCLDBVESU-UHFFFAOYSA-N 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 230000035606 childbirth Effects 0.000 abstract 1
- 229940124558 contraceptive agent Drugs 0.000 abstract 1
- 239000003433 contraceptive agent Substances 0.000 abstract 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- VONWDASPFIQPDY-UHFFFAOYSA-N dimethyl methylphosphonate Chemical compound COP(C)(=O)OC VONWDASPFIQPDY-UHFFFAOYSA-N 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 230000012173 estrus Effects 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 208000021822 hypotensive Diseases 0.000 abstract 1
- 230000001077 hypotensive effect Effects 0.000 abstract 1
- 230000006698 induction Effects 0.000 abstract 1
- 150000002596 lactones Chemical class 0.000 abstract 1
- 150000004702 methyl esters Chemical class 0.000 abstract 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 abstract 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 abstract 1
- 230000035935 pregnancy Effects 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 229910000104 sodium hydride Inorganic materials 0.000 abstract 1
- 239000012312 sodium hydride Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 abstract 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 1
- 229920002554 vinyl polymer Polymers 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
- C07D307/935—Not further condensed cyclopenta [b] furans or hydrogenated cyclopenta [b] furans
-
- 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
- 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
- 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
-
- 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
- C07F9/4015—Esters of acyclic unsaturated acids
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)
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB48131/70*2A GB1356581A (en) | 1970-10-09 | 1970-10-09 | Cyclopentane derivatives |
| ZA716270A ZA716270B (en) | 1970-10-09 | 1971-09-20 | Cyclopentane derivatives |
| HUIE478A HU163414B (ja) | 1970-10-09 | 1971-09-21 | |
| IL37821A IL37821A0 (en) | 1970-10-09 | 1971-09-28 | Cyclopentane derivatives |
| ZM142/71A ZM14271A1 (en) | 1970-10-09 | 1971-10-01 | Cyclopentane derivatives |
| SU1702653A SU439962A1 (ru) | 1971-10-04 | Способ получени производных простанкарбоновой кислоты | |
| ES395814A ES395814A1 (es) | 1970-10-09 | 1971-10-07 | Procedimiento para la obtencion de derivados del acido prostanoico. |
| AU34335/71A AU3433571A (en) | 1970-10-09 | 1971-10-07 | Cyclopentane derivatives |
| FR7136366A FR2110335B1 (ja) | 1970-10-09 | 1971-10-08 | |
| NL7113880A NL7113880A (ja) | 1970-10-09 | 1971-10-08 | |
| BE773728A BE773728A (fr) | 1970-10-09 | 1971-10-08 | Derives du cyclopentane |
| DE19712150361 DE2150361A1 (de) | 1970-10-09 | 1971-10-08 | Prostanoesaeurederivate |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB48131/70*2A GB1356581A (en) | 1970-10-09 | 1970-10-09 | Cyclopentane derivatives |
| GB181471 | 1971-01-14 | ||
| GB554371 | 1971-02-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1356581A true GB1356581A (en) | 1974-06-12 |
Family
ID=27253947
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB48131/70*2A Expired GB1356581A (en) | 1970-10-09 | 1970-10-09 | Cyclopentane derivatives |
Country Status (9)
| Country | Link |
|---|---|
| BE (1) | BE773728A (ja) |
| DE (1) | DE2150361A1 (ja) |
| ES (1) | ES395814A1 (ja) |
| FR (1) | FR2110335B1 (ja) |
| GB (1) | GB1356581A (ja) |
| HU (1) | HU163414B (ja) |
| IL (1) | IL37821A0 (ja) |
| NL (1) | NL7113880A (ja) |
| ZM (1) | ZM14271A1 (ja) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2015134801A (ja) * | 2015-03-09 | 2015-07-27 | テックフィールズ バイオケム カンパニー リミテッド | 非常に高い皮膚浸透率を有するプロスタグランジン及び関連化合物の正荷電水溶性プロドラッグ |
| JP2016074730A (ja) * | 2016-01-08 | 2016-05-12 | テックフィールズ バイオケム カンパニー リミテッド | 非常に高い皮膚浸透率を有するプロスタグランジン及び関連化合物の正荷電水溶性プロドラッグ |
| JP7141025B1 (ja) | 2021-11-11 | 2022-09-22 | エルデシエロ プライベート リミテッド | 化合物、組成物、方法、及び製造方法 |
| US11555014B2 (en) | 2006-10-02 | 2023-01-17 | Techfields Pharma Co., Ltd. | High penetration prodrug compositions of prostaglandins and related compounds |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3887587A (en) * | 1972-04-17 | 1975-06-03 | Pfizer | Synthesis of prostaglandins of the one-series |
| DE2317019A1 (de) * | 1972-04-27 | 1973-11-08 | Upjohn Co | Neue 4,5-didehydro-prostaglandine |
| US3954741A (en) * | 1972-06-07 | 1976-05-04 | Pfizer Inc. | N-substituted prostaglandin carboxamides |
| GB1520522A (en) * | 1975-06-16 | 1978-08-09 | Ono Pharmaceutical Co | 16-methyleneprostaglandins |
| US6420422B1 (en) | 1987-09-18 | 2002-07-16 | Sucampo Pharmaceuticals, Inc. | Ocular hypotensive agents |
| US5236907A (en) * | 1988-10-01 | 1993-08-17 | R-Tech Ueno Ltd. | Ocular hypotensive agents |
| US5194429A (en) * | 1988-10-01 | 1993-03-16 | K.K. Ueno Seiyaku Oyo Kenkyujo | Ocular hypotensive agents |
| ATE111736T1 (de) * | 1988-10-01 | 1994-10-15 | R Tech Ueno Ltd | Okulare hypotensive mittel. |
-
1970
- 1970-10-09 GB GB48131/70*2A patent/GB1356581A/en not_active Expired
-
1971
- 1971-09-21 HU HUIE478A patent/HU163414B/hu unknown
- 1971-09-28 IL IL37821A patent/IL37821A0/xx unknown
- 1971-10-01 ZM ZM142/71A patent/ZM14271A1/xx unknown
- 1971-10-07 ES ES395814A patent/ES395814A1/es not_active Expired
- 1971-10-08 FR FR7136366A patent/FR2110335B1/fr not_active Expired
- 1971-10-08 BE BE773728A patent/BE773728A/xx unknown
- 1971-10-08 NL NL7113880A patent/NL7113880A/xx unknown
- 1971-10-08 DE DE19712150361 patent/DE2150361A1/de active Pending
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11555014B2 (en) | 2006-10-02 | 2023-01-17 | Techfields Pharma Co., Ltd. | High penetration prodrug compositions of prostaglandins and related compounds |
| JP2015134801A (ja) * | 2015-03-09 | 2015-07-27 | テックフィールズ バイオケム カンパニー リミテッド | 非常に高い皮膚浸透率を有するプロスタグランジン及び関連化合物の正荷電水溶性プロドラッグ |
| JP2016074730A (ja) * | 2016-01-08 | 2016-05-12 | テックフィールズ バイオケム カンパニー リミテッド | 非常に高い皮膚浸透率を有するプロスタグランジン及び関連化合物の正荷電水溶性プロドラッグ |
| JP7141025B1 (ja) | 2021-11-11 | 2022-09-22 | エルデシエロ プライベート リミテッド | 化合物、組成物、方法、及び製造方法 |
| WO2023085135A1 (ja) * | 2021-11-11 | 2023-05-19 | エルデシエロ プライベート リミテッド | 化合物、組成物、方法、及び製造方法 |
| JP2023071523A (ja) * | 2021-11-11 | 2023-05-23 | エルデシエロ プライベート リミテッド | 化合物、組成物、方法、及び製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| SU439962A3 (ru) | 1974-08-15 |
| ZM14271A1 (en) | 1972-06-21 |
| HU163414B (ja) | 1973-08-28 |
| ES395814A1 (es) | 1975-03-01 |
| FR2110335B1 (ja) | 1975-06-06 |
| FR2110335A1 (ja) | 1972-06-02 |
| IL37821A0 (en) | 1971-11-29 |
| DE2150361A1 (de) | 1972-04-13 |
| NL7113880A (ja) | 1972-04-11 |
| BE773728A (fr) | 1972-04-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| CSNS | Application of which complete specification have been accepted and published, but patent is not sealed |