DE2638677A1 - Neue cyclopentanderivate, verfahren zu ihrer herstellung und pharmazeutische zusammensetzungen - Google Patents
Neue cyclopentanderivate, verfahren zu ihrer herstellung und pharmazeutische zusammensetzungenInfo
- Publication number
- DE2638677A1 DE2638677A1 DE19762638677 DE2638677A DE2638677A1 DE 2638677 A1 DE2638677 A1 DE 2638677A1 DE 19762638677 DE19762638677 DE 19762638677 DE 2638677 A DE2638677 A DE 2638677A DE 2638677 A1 DE2638677 A1 DE 2638677A1
- Authority
- DE
- Germany
- Prior art keywords
- radical
- compound
- formula
- general formula
- hydrogen atom
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title description 4
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical class C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 87
- -1 alkyl radical Chemical class 0.000 claims description 56
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 25
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 150000003254 radicals Chemical class 0.000 claims description 20
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 14
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 13
- 150000003839 salts Chemical group 0.000 claims description 13
- 239000003513 alkali Substances 0.000 claims description 10
- ORTFAQDWJHRMNX-UHFFFAOYSA-M oxidooxomethyl Chemical compound [O-][C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-M 0.000 claims description 10
- 239000002585 base Substances 0.000 claims description 9
- 239000003638 chemical reducing agent Substances 0.000 claims description 8
- 150000007513 acids Chemical class 0.000 claims description 7
- 239000004480 active ingredient Substances 0.000 claims description 7
- 238000010992 reflux Methods 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 6
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 150000001340 alkali metals Chemical group 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical compound OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 claims description 4
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 claims description 3
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- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 claims description 3
- 150000008065 acid anhydrides Chemical class 0.000 claims description 2
- ISQVBYGGNVVVHB-UHFFFAOYSA-N cyclopentylmethanol Chemical compound OCC1CCCC1 ISQVBYGGNVVVHB-UHFFFAOYSA-N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
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- 125000003118 aryl group Chemical group 0.000 claims 1
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- 239000008101 lactose Substances 0.000 description 1
- 125000000400 lauroyl group Chemical group O=C([*])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])C([H])([H])[H] 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- YECBIJXISLIIDS-UHFFFAOYSA-N mepyramine Chemical compound C1=CC(OC)=CC=C1CN(CCN(C)C)C1=CC=CC=N1 YECBIJXISLIIDS-UHFFFAOYSA-N 0.000 description 1
- 229960000582 mepyramine Drugs 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229960001186 methysergide Drugs 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 208000015994 miscarriage Diseases 0.000 description 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 208000013465 muscle pain Diseases 0.000 description 1
- 239000002687 nonaqueous vehicle Substances 0.000 description 1
- 125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229960003418 phenoxybenzamine Drugs 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 230000002997 prostaglandinlike Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- STECJAGHUSJQJN-FWXGHANASA-N scopolamine Chemical compound C1([C@@H](CO)C(=O)O[C@H]2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-FWXGHANASA-N 0.000 description 1
- 229960002646 scopolamine Drugs 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229940001593 sodium carbonate Drugs 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 208000000995 spontaneous abortion Diseases 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000006000 trichloroethyl group Chemical group 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 208000019553 vascular disease Diseases 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C35/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic
- C07C35/06—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic containing a five-membered rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7526617A FR2321876A1 (fr) | 1975-08-29 | 1975-08-29 | Nouveaux derives cyclopentaniques, leur procede de preparation et leur application comme medicaments |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2638677A1 true DE2638677A1 (de) | 1977-03-10 |
Family
ID=9159454
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762638677 Withdrawn DE2638677A1 (de) | 1975-08-29 | 1976-08-27 | Neue cyclopentanderivate, verfahren zu ihrer herstellung und pharmazeutische zusammensetzungen |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4072755A (cg-RX-API-DMAC7.html) |
| JP (1) | JPS5231050A (cg-RX-API-DMAC7.html) |
| BE (1) | BE845599A (cg-RX-API-DMAC7.html) |
| CA (1) | CA1087201A (cg-RX-API-DMAC7.html) |
| CH (1) | CH614923A5 (cg-RX-API-DMAC7.html) |
| DE (1) | DE2638677A1 (cg-RX-API-DMAC7.html) |
| DK (1) | DK388276A (cg-RX-API-DMAC7.html) |
| FR (1) | FR2321876A1 (cg-RX-API-DMAC7.html) |
| GB (1) | GB1526499A (cg-RX-API-DMAC7.html) |
| IE (1) | IE44384B1 (cg-RX-API-DMAC7.html) |
| LU (1) | LU75675A1 (cg-RX-API-DMAC7.html) |
| NL (1) | NL7609645A (cg-RX-API-DMAC7.html) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2046069C (en) * | 1990-07-10 | 2002-04-09 | Ryuji Ueno | Treatment of inflammatory diseases with 15-keto-prostaglandin compounds |
| JP3053872B2 (ja) * | 1994-06-23 | 2000-06-19 | フイルメニツヒ ソシエテ アノニム | （＋）−（１ｒ）−シス−３−オキソ−２−ペンチル−１−シクロペンタン酢酸の製造法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3974200A (en) * | 1969-03-14 | 1976-08-10 | The Upjohn Company | Racemic prostaglandins of the 2-series and analogs thereof |
| US3880906A (en) * | 1971-05-24 | 1975-04-29 | Alza Corp | Novel compounds related to prostaglandins |
| US3993674A (en) * | 1973-04-20 | 1976-11-23 | American Cyanamid Company | Novel prostaglandins |
-
1975
- 1975-08-29 FR FR7526617A patent/FR2321876A1/fr active Granted
-
1976
- 1976-08-24 US US05/717,049 patent/US4072755A/en not_active Expired - Lifetime
- 1976-08-27 DK DK388276A patent/DK388276A/da not_active Application Discontinuation
- 1976-08-27 JP JP51101777A patent/JPS5231050A/ja active Pending
- 1976-08-27 BE BE170142A patent/BE845599A/xx not_active IP Right Cessation
- 1976-08-27 IE IE1924/76A patent/IE44384B1/en unknown
- 1976-08-27 CH CH1089876A patent/CH614923A5/xx not_active IP Right Cessation
- 1976-08-27 GB GB35781/76A patent/GB1526499A/en not_active Expired
- 1976-08-27 LU LU75675A patent/LU75675A1/xx unknown
- 1976-08-27 DE DE19762638677 patent/DE2638677A1/de not_active Withdrawn
- 1976-08-27 CA CA260,003A patent/CA1087201A/fr not_active Expired
- 1976-08-30 NL NL7609645A patent/NL7609645A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| LU75675A1 (cg-RX-API-DMAC7.html) | 1977-04-27 |
| IE44384L (en) | 1977-02-28 |
| US4072755A (en) | 1978-02-07 |
| FR2321876A1 (fr) | 1977-03-25 |
| DK388276A (da) | 1977-03-01 |
| NL7609645A (nl) | 1977-03-02 |
| CA1087201A (fr) | 1980-10-07 |
| IE44384B1 (en) | 1981-11-04 |
| BE845599A (fr) | 1977-02-28 |
| FR2321876B1 (cg-RX-API-DMAC7.html) | 1979-09-14 |
| CH614923A5 (cg-RX-API-DMAC7.html) | 1979-12-28 |
| JPS5231050A (en) | 1977-03-09 |
| GB1526499A (en) | 1978-09-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8141 | Disposal/no request for examination |